


The Substitute

by LandlessBud



Series: prohibition era [1]
Category: Newsies (1992), Newsies - All Media Types, Newsies!: the Musical - Fierstein/Menken
Genre: 1920s AU, Alcohol, Alternate Universe - Historical, Alternate Universe - Mob, Black Albert DaSilva, Black Buttons, Black Crutchie, Black Jack Kelly, Black Mush Meyers, Black Smalls, Black Specs, Bootlegging AU, F/F, Gun Violence, Historical References, Irish Racetrack Higgins, Italian Spot Conlon, Jewish David Jacobs, Jewish Katherine Plumber Pulitzer, Jewish Sarah Jacobs, M/M, Mafia AU, Mention of gun violence, Other Additional Tags to Be Added, Period-Typical Racism, Prohibition AU, arnold rothstein is important but never actually appears, slight historical inaccuracy at times, speakeasy au
Language: English
Status: Completed
Published: 2020-06-25
Updated: 2020-08-08
Packaged: 2021-03-03 23:48:15
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 24,555
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24904087
Author URL: https://archiveofourown.org/users/LandlessBud/pseuds/LandlessBud
Summary: “I—I’m David,” he mumbled, eyes on the floor. “David Jacobs. Shit, I’ve already fucked this up. First day in the mob I didn’t know my father was a part of and I’m already bad at it.”It's 1924, and Jack Kelly's bootlegger is late.
Relationships: David Jacobs/Jack Kelly, Sarah Jacobs/Katherine Plumber Pulitzer, Spot Conlon/Racetrack Higgins, background Smalls/Buttons
Series: prohibition era [1]
Series URL: https://archiveofourown.org/series/1876714
Comments: 153
Kudos: 106





	1. Chapter 1

**Author's Note:**

  * For [PenzyRome](https://archiveofourown.org/users/PenzyRome/gifts).



The runner was late.

Rothstein’s runner was never late to _Miss Medda’s_. A seemingly gentle older man, Mayer Jacobs was very punctual and very discreet. Perhaps that’s how he got away with bootlegging for Arnold Rothstein, of all people, for so long. Jack Kelly didn’t know, and Jack knew he wasn’t supposed to know. 

But Mayer was never late. Jack had watched the seconds tick away on that ancient grandfather clock in the corner that Miss Medda insisted upon keeping in the joint for far too long. Something had to be very, very wrong for it to be four in the morning with no sign of his two o’clock sharp delivery.

The end of the cigarette burning his fingertips brought Jack back to reality as he barely made out the sound of faint knocking on the delivery door. Odd. Mayer knew not to knock. Jack left the cash in the lockbox in the flowerpot, and Mayer left the neatly wrapped crates inside the storm door that only he had a key to. It was a flawless operation, and Jack had come to appreciate the old man’s kindness on the off chance that they actually came in contact. But where was he? And who could possibly be knocking on the door?

Jack stubbed out his cigarette, cocked his pistol, and prepared for the worst. Miss Medda may have been the headliner of the speakeasy, but he’d been running the place since it went underground four years ago in 1920. Medda didn’t want a hand in the nasty business she knew she’d have to engage with in order to keep the booze flowing, so Jack had volunteered to take over and negotiate with the mob. And negotiate he did. Jack had weaseled with Rothstein enough that Medda herself was still the official proprietor of the club, and Rothstein supplied them with the good stuff.

Jack crept towards the back door, gun trained straight ahead of him. The knocking dropped off briefly, then continued again. Whoever was at his door must be inexperienced—the police would’ve busted right on in. It had to be someone’s lackey, and Jack hoped that it was just another one of Rothstein’s men. Though he knew Costello and Legs were allied with Rothstein on paper, he didn’t trust that they wouldn’t work to backstab Rothstein and leave Jack out to dry. 

The person at the door knocked again. Jack had a feeling it could be a confused pedestrian wandering through the wrong alley, but he knew he couldn’t be too careful. So he pried open the storm door, gun leading, and peeked.

Mayer Jacobs was nowhere to be seen.

Instead, a tall, lanky young man stood outside his door, clearly frightened.

“Who are you?” Jack growled, gun still trained on the man. “You lost?”

The man started, clearly not expecting to be talked to. Strange.

Jack opened the door a little further and focused his best I’m-A-Busy-And-Important-Man glare on the stranger. “Harlem’s a little far north for ya, pal. Start talking.”

“You’re Jack, right?” the man peeped, somewhat shellshocked.

“Who’s askin’?” Jack snapped, pointing his pistol at the man’s head. “This ain’t a good part of town for a white man like yourself. Scram.”

“I—I’m Mayer’s son. Here for Rothstein. I got lost. First day,” the man eked out. “I, uh. I’ve got your delivery.”

Jack pitied this clearly green man. Strange that he hadn’t been in business with his father for longer. Jack’s curiosity overtook his caution, but not so much that he even thought of lowering his pistol. “Bring it in. I can show you the ropes.”

The man was surprisingly muscular for his wiry stature. He lifted his stack of crates and followed Jack into the abyss of _Miss Medda’s_.

“Don’t let the door slam behind you,” Jack softly cautioned. He guided the man to the back storeroom, disguised behind some of the many curtains of Miss Medda’s stage. “You can set them here,” he instructed as the man set down the crates with relief. “Come with me. I got a few questions for you.” 

Jack led the man to the two stools left from the evening’s act on the stage. He sat on one and gestured for the new runner to take a seat on the other. The man deflated as he sat.

Jack knew he could take advantage of the runner’s greenness, but he didn’t want to push him too far. Just a gentle prod should get him going. “First: where’s Mayer?”

“He, uh. He got hurt on one of his other runs. Asked me to take over.”

Jack mulled over the thought. It sounded plausible enough. And this man bore a decent enough resemblance to Mayer that Jack was fairly certain he wasn’t lying. Judging by his running mouth, Jack doubted that the man knew _how_ to lie. “Alright, pal.” Jack kept his tone impassive, the way he’d learned after being on the wrong side of one of Rothstein’s lackeys early on. “Got a name besides Mayer’s Son?”

The runner actually had the audacity to blush at this. “I—I’m David,” he mumbled, eyes on the floor. “David Jacobs. Shit, I’ve already fucked this up. First day in the mob I didn’t know my father was a part of and I’m already bad at it.”

“Whoa, whoa, Davey—slow down. Mouthin’ off like that’ll get you lead poisoning real quick. Real walkin’ mouth you are.” Jack didn’t know what it was about this Davey that made him want to keep the runner around. As kind as Mayer could be when times were hard, Davey was a breath of fresh air. Jack rarely had a chance to actually socialize with people his own age, as bartending was a hectic job and most of his patrons came to see Miss Medda’s performances, not him. He spotted the occasional mobster in the crowd and could talk to a couple thanks to his ties to Rothstein, but otherwise he kept to himself. 

“It’s—Fuck. Pa told me not to argue.”

“I’ll call you Mouth. How’s that?”

Davey grimaced for a moment, then nodded.

“Okay, pal. Mouth. Here’s the deal. Your pop knew how to keep this a quick and clean operation. You gotta do the same, or you’ll be worse off than him in a matter of minutes. Got it?”

Jack worried he was being a bit hard on Davey, but bootlegging was no laughing matter. The minute the cops caught wind of _Miss Medda’s_ being open and serving booze, he was done for. They wouldn’t be kind enough to throw him in a cell for the rest of his life—that was a privilege reserved for white violators of the Volstead Act. The speakeasy was his life. If he lost it, he was a goner. 

Davey nodded mutely.

“You got his key?” Jack asked. “Didn’t know he had a replacement, so I don’t have a copy.”

Davey nodded again, pulling a chain out from underneath the neck of his shirt.

“Good. That unlocks that door you were pounding on so loudly. Don’t do that again—you’re lucky you didn’t get caught tonight. Unlock the door, drop the booze inside, and hightail it on out. Once you hit Central Park, you’re golden. Don’t wanna be caught dead out here, white boy. Get me?”

Davey nodded.

“I know you got a mouth, boy. Use it.” Jack said, fed up with being the only participant in this conversation.

“Got it,” Davey mumbled. He paused. “I should lock the door on the way out, right?”

“Got no brain in that head of yours, Mouth?” Jack knew he shouldn’t let his temper get ahead of him, but something in Davey brought his emotions forward. “You leave it unlocked, we’re all dead, and Rothstein has your head _and_ your father’s.”

Davey cowered. “Um, okay. So. I unlock the door, drop the booze, lock the door, and scram?”

“Two AM sharp every Sunday. Cash’s in the lockbox in the flowerpot. I assume you know who to take it to. I shouldn’t see hide nor hair of you if you’re doing your job right.”

Davey nodded, blushing but seemingly almost disappointed by this. Jack couldn’t understand him. You didn’t get into the mob to make friends—you did it to protect yourself and your family. So maybe being a runner could be somewhat lonely, but the boss would get Davey matched up with some nice girl sooner or later that’d help him climb the ranks if he played his cards right. As klutzy and awkward as he appeared, Jack could tell Davey was intelligent under all that anxiety.

Jack shook himself out of his thoughts. Four AM was not the ideal time to contemplate the criminal future of a man (barely—Davey couldn’t be any older than Jack’s 25 years) he had met ten minutes ago. “You’ll get used to it, kid. Trust me.”

“Don’t call me kid,” Davey snapped back. “You ain’t that old yourself. Also, how’re you gonna know when I drop the booze off?”

“You’ll be on time. The less we see of each other, the better. Capisce?”

Davey blinked.

“Capisce, y’know?”

Davey blinked again.

“Damnit, I’ve been around the Italians too much. Be on time. I should see no trace of you when I check the back at 2:01.”

“So much for a good post-Shabbos sleep,” Davey grumbled under his breath.

“What was that?” Jack asked innocently, pretending not to understand.

Davey, intelligently, held his tongue.

“That’s what I thought. I’ll see your next dropoff next week. Now get outta here before anyone notices you’re gone.”

Davey slid off his stool and raced out the way he came. Jack nearly didn’t catch Davey turning back for one last look. He tensed until he heard Davey’s key turn in the lock, then double checked all the locks and headed upstairs to the shoebox apartment Miss Medda let him rent for free. 

As he stripped down and prepared for bed, Jack couldn’t stop thinking about that look of disappointment in Davey’s doe eyes. The poor kid may be green now, but he’d shape up soon enough.

Jack didn’t think about the sinking feeling in his stomach when he realized he most likely wouldn’t see Davey ever again.

* * *

Jack had just finished mixing his thirteenth highball of the night and shoved it across the counter to a far-too-eager patron when a couple of familiar faces sidled up to the bar. 

“Jacky boy!” the notorious Racetrack Higgins cheered. “It’s been too long!”

“Race! Spot!” Jack called back over the din of the crowded speakeasy. “How’re you doing, fellas?”

“Get me an old fashioned, then I’ll talk,” Spot Conlon groused.

Jack obliged, never turning his back to the dangerous pair. As friendly as he was with Race and Spot, he knew he still couldn’t quite trust them. Jack slid the drink across the counter. Spot sniffed it and took a sip.

“Nice one, Jackie. Rothstein getcha the good shit again?”

“You know him better than I do, pal,” Jack said. “Think he’d do anything less? Variety’s the spice of life, and his guys don’t want to go to the same bar every night.”

Jack preferred to keep his nose out of mafia business, mostly out of a sense of self-preservation, but he wouldn’t let his two favorite mobsters on to that. He did, however, enjoy hearing their gossip and learning far more from it than he should.

Race snorted out a laugh. “Legs’d be gone in an instant if Rothstein stopped importing Scotch. Rothstein’s smart enough to know that, ya dewdropper. Now get me some of that panther piss.”

“This shit’s authentic, you goon,” Jack griped. He still pulled out a bottle of scotch, fresh from Davey’s most recent run. Jack hadn’t caught more than a brief glimpse of his new runner since they had first met a couple weeks ago. Davey was quickly getting slicker and harder to catch. Good. Pouring the whiskey into a scotch glass, Jack shook himself out of his reverie. Why should he care about a runner he barely knew?

“What’s got you so out of it?” Race prodded, catching the far-away look in Jack’s eyes.

Jack laughed weakly and passed Race his drink. “Everything’s jake. What’re you on about?”

“Wait, wait. Race. Hold on. You telling me you ain’t heard the news?” Spot said, a devious glint in his eye.

Jack did not like the sound of this. He pulled out a towel and began scrubbing at the bar, his cheeks burning.

“What news? Costello loop you in on something I don’t know?” Race elbowed his companion jovially. “Spill.”

“I hear Jackie here’s got himself a new runner. Some egg going by Mouth, according to the fellas on the street.”

Jack was secretly thrilled that Davey had taken on the moniker he gave him. A small grin tugged at the corners of Jack’s mouth, but he wouldn’t let that information out so easily.

“That so?” Race could tell something was up. 

“Seems he’s younger and spryer than Jack’s old runner. What happened to him anyway, Mac?” Spot asked.

Jack scratched the back of his neck. There really was no keeping any secrets from these two. Hell, he was fairly certain they’d be happy to hogtie him and hold him at gunpoint to get information out of him. 

Race reached over and snapped Jack’s suspender. “Hey, pal. What’s going on?”

“Okay, okay. Old man got hurt, his boy got involved. Didn’t think the poor kid’d stand a chance, seeing as he wasn’t raised in the family business, but he seems to be getting along fine,” Jack said quietly, quickly glancing over the crowd to ensure he wouldn’t be overheard by the wrong people. Luckily, Race and Spot seemed to be the only mobsters in the joint that night.

“Glad to hear it. Hopefully we’ll be making his acquaintance soon,” Spot replied.

Jack laughed nervously. He wasn’t sure Davey would survive an interaction with Spot and Race, let alone their strange intersection of the Italian and Irish mobs. Granted, Jack was a civilian trying to make ends meet, and Davey had just been thrown headfirst into the Jewish mob himself, so he really wasn’t one to judge. Perhaps closer ties to other mobsters would be a good thing for inexperienced, terrified Davey.

“Hey, professor!” Race snapped dramatically in Jack’s face. “Hit me!”

He poured Race another drink with a small chuckle, then returned his focus to serving the steadily increasing line of patrons at the bar, daydreaming (though he wouldn’t admit it) all the while.

“ _...I’m gonna hold it until you meet some of my demands,_ ” Miss Medda crooned, closing her set for the night. Jack cheered from the bar for her and the band.

“Thank you all!” she called from the stage. “Now get your sorry asses on home! And don’t get caught! Good night!”

Jack plastered his cheeky Customer Service Grin across his face as he waved the patrons out. Miss Medda was the shining star of the club, and he was the hotsy-totsy wallpaper. With his sleek vest, bowtie, and classy mustache, Jack could almost pass as a patron himself. He pulled out his pocket watch. One AM. Perfect. He’d have plenty of time to sweep up, reorganize the bar, and triple check the locks before getting to bed at a perfectly reasonable time to wake up and repeat his routine all over again. 

Casting a glance over the club to ensure its emptiness, Jack began putting chairs on top of the tables to prepare to sweep. Distracted by unreasonable worries, he didn’t notice Miss Medda approaching him from backstage.

“You never give yourself a break, do you?” she said, concerned.

He started. “Gotta pay the bills somehow, Miss.”

She sighed and took his face in her hands. “Jack Kelly, you sap. You’re gonna run yourself ragged if you keep this up.”

“I ain’t got much else to do,” Jack replied. “Hard enough just living as it is.”

Miss Medda pressed a motherly kiss to his forehead. “Take the rest of tonight off, son. I can take care of the club. You go pay a visit to your guests.”

Jack’s jaw dropped. “Guests?”

By the time he had processed Miss Medda’s instructions, she had left Jack alone. Wordlessly, he headed up to the stage and drew back the curtain.

“Howdy.”

“Took you long enough, amico.”

None other but Racetrack Higgins and Spot Conlon sat at the makeup counter.

“You shouldn’t be here.” Jack’s sensibilities as the proprietor of a highly illegal business outweighed his regard for his… acquaintances? Friends? He figured he could call Spot and Race friends. They were the only people he talked to on a regular basis besides Miss Medda and the patrons of his bar.

“Think we don’t know how to cover our own tracks, pal?” Jack was rarely intimidated by Race, who appeared silly and happy-go-lucky on the surface, but his sharp retort shot a dagger of fear into Jack’s heart. These were men who dealt in darker dealings than Jack: men who most likely killed for a living and had no qualms about it. 

Jack put his hands up in defeat. “Okay, okay. What do you want?”

Spot still had a dark glint in his eye that unsettled Jack. “The Mouth’s coming tonight, ain’t he?”

“And what if he were?” Jack replied cagily. He couldn’t hand everything to the mob on a silver platter.

“It’s about time we make his acquaintance,” Race said, cracking his knuckles. Jack may have shrank back a little, but he wouldn’t admit that to anyone. “It’s Sunday, right? Your deliveries always come on Sundays.”

Jack didn’t want to think about how they knew that.

“So, Jacky boy.” Spot gave him a sharp-toothed grin. “We’re gonna hang around ‘til the Mouth shows.”

Jack’s spine stiffened. He knew that Spot and Race wouldn’t do anything to Davey, but… there was something about having Davey to himself that he liked. So maybe he’d been planning a way to see Davey again, but that was none of Spot and Race’s business. Jack was not particularly pleased about their forcing his hand before he was ready.

“It’ll be a while.” Jack knew talking back was playing with fire, but at that point he was too exhausted to care.

“We’ll wait.”

Spot sat silently, his gaze unnaturally fixed upon Jack.

After a few minutes, Race began fidgeting in his seat and fiddling with his hands. Spot patted Race’s knee gently, still focused on Jack. Interesting. Spot didn’t seem to be the jewelry-wearing type, but Jack knew better than to comment on the new ring on his right hand.

**Notes for the Chapter:**

> hello!! hope you all enjoyed this! it's been FOREVER since I've written anything on my own. big shoutout to penzy for waiting literally a month for this fic to actually happen bc i started writing this for her birthday in may lol and big shoutout to ella (@illinoise on ao3, livingchancy on The Tungle) for reading through this!!  
> a bit of historical context: arnold rothstein was new york's most influential mobster in the early 20s. after his death nyc had to revamp its entire judicial system bc he had bought out so much of it! most of his power came from his work in bootlegging and running speakeasies.  
> the song Medda sings in this chapter is Down Hearted Blues by Bessie Smith. you can listen to it [here](https://youtu.be/go6TiLIeVZA)!  
> follow me on tumblr! i'm landlessbud!  
> (PS: if you liked this please RB [this post](https://landlessbud.tumblr.com/post/621857494037299200/the-substitute-iim-david-he-mumbled-eyes-on)!!! and please please comment! i'd love to hear y'all's thoughts!)


	2. Chapter 2

**Summary for the Chapter:**

> Jack just can't seem to say no.

Jack jolted upright at the clock’s chime. Only a half hour until Davey showed. His anxiety heightened as the minutes ticked on. Jack didn’t think Spot and Race knew exactly when Davey would come, but then again they had eyes and ears in unfathomable places.

Spot laughed darkly, catching Jack’s agitation. “Mouth’s coming soon, huh?”

Jack pursed his lips. “Perhaps.”

Race sat mutely, tapping his fingers on his lap. Jack caught the glint of a ring on his right hand. He was starting to get an inkling as to why Spot and Race never showed up to  _ Miss Medda’s _ separately.

Minutes and seconds slowly ticked away on the old grandfather clock Miss Medda liked to keep backstage. At precisely 1:50 AM, Spot stood up.

“C’mon Race, Jacky boy. We’re gonna go for a little walk.” He left no room for questions as he and Race took Jack by the biceps and frogmarched him to his own back door.

Race turned to Jack. “You’re greeting the Mouth. Get him inside, and we’ll take it from there. Capisce?”

“Capisco,” Jack grumbled. He may not have wanted to get involved in any high-up mafia business, but that didn’t mean Jack hadn’t picked up a few Italian phrases here and there from Spot (and, occasionally, Race, when he had had a little too much.).

Spot and Race slipped out of view of the door. The club’s darkened, silent interior weighed Jack down like a heavy blanket as he stepped outside. He couldn’t shake the feeling that he was being watched. Not just by Spot and Race, but by something much more sinister. Second after oppressive second tick-tocked away as he leaned against the wall and attempted to build up some semi-legitimate feigned nonchalance. Jack wished he had the courage to keep Spot and Race from Davey, but the small resistance he had already put up had seemed to stretch them to their limits. Being Black and breaking the law was tricky enough as it was—Jack didn’t want to add the pressure of mafia suspicion on top of that. 

Jack heard Davey before he saw him. The truck was fairly quiet, and the noise of the parties in the apartments above helped disguise the groaning engine. His fingers twitched. Perhaps he should’ve brought a cigarette out with him—it would’ve been a convincing excuse should the cops have shown up. Then again, the light would have exposed his hiding spot and Davey would bolt. 

A lumber truck backed into the alley slowly. Jack had never actually watched his runners bring in the booze before—it was safer to let them take care of the delivery and deal with it once it was inside the club. Plausible deniability was important, though Jack doubted his word would ever hold up in court. The driver kept the engine running as a tall, lean figure jumped out of the passenger seat and jogged to the back. Jack was still invisible to them, hidden in the shadows beside the door. The figure, ostensibly Davey himself, pulled the end off the lumber pile, revealing crates with glittering glass bottles inside. So that was how they got the liquor from the Lower East Side to Harlem. Clever.

Jack had been mulling in his thoughts long enough that he almost didn’t catch the way Davey’s wiry frame practically rippled with muscle as he stacked several crates in preparation to bring them inside. His tank top (it was a hot summer night, after all) certainly didn’t help the allure of his nonchalant, liquid-smooth movement at all.

Jack shook himself out of his thoughts. Davey, who had just set down another crate on an already remarkably tall pile, started. Fuck. Jack’s trusty pistol, always in his back pocket, had hit the wall. Davey whipped out his own pistol with practiced ease and pointed it directly towards where Jack was hidden in the shadows.

“Don’t make me come find you,” he growled, approaching slowly, gun first.

Jack froze. His heart thudded in his chest. He didn’t realize how quickly Davey would become hardened by his time in the mob.

“I’m not going to repeat myself,” Davey threatened. “You got five seconds before you’ve earned yourself lead poisoning.”

Jack wisely left his pistol in his pocket, raised his hands, and stepped out into the dim light of the alleyway.

Several emotions fleetingly crossed Davey’s face before he relaxed and tucked his pistol back into the waistband of his pants. He plastered an easy grin on his face. “Jack! To what do I owe the pleasure?” he asked, loud enough for Jack to hear but quiet enough that his voice didn’t echo through the alley.

“We, uh. We’ve got some negotiations to talk, Mouth. Why don’t you bring those inside?” Jack said, gesturing to the stack of crates beside Davey. “I can help if you’d like.”

Davey paused. Jack hoped he didn’t catch on.

“I guess I wouldn’t mind some help,” Davey finally replied, measured. “Can you take these? I’ve got a few more to get out of the back.”

Jack nodded, then picked up the stack of crates and headed to the back door. Propping it open for Davey, he stepped inside.

Spot and Race had their guns trained on him. “Whoa, boys,” Jack called. “It’s just me. Mouth’s coming in next.”

They relaxed their posture slightly as Jack passed by them and continued towards the storeroom, though he could hear a pistol being cocked behind him as he reached the stage. Jack continued down the stairs to the cellar, feeling himself sink into the tension like it was quicksand. He worried he may have accidentally brought Davey a death sentence.

_ THUNK. _ Jack heard a gasp and a clatter accompanying the sound. He set down his crates as quickly as possible and raced back to where he knew Spot and Race were stationed.

Davey stood, shaking, pale as a ghost. Race and Spot had dropped their guns. A small pool of liquor was forming on the floor. Jack felt as if he had missed out on something. Feigning a cool, collected demeanor, he broached the subject. “So, boys. What’s going on here? You trying to scare my runner off?”

Race squeaked incoherently.

“Nice to finally meet the infamous Mouth,” Spot said, looking Davey up and down. Something flickered in his eyes, but Jack couldn’t figure it out. It was probably something it’d be better for him not to know, anyway. 

Davey turned to Jack, fear and betrayal painted across his face. “Was this the only reason you offered to help?”

Jack opened his mouth, fish-like, then closed it again. “I—that is, uh—y’know, you people”—he gestured to Race and Spot—“are really hard to say no to.” He hoped Davey would get his message through that. And, to be fair, he  _ had _ been trying to figure out a sufficient excuse to see Davey again. Race and Spot had simply… accelerated the process.

“I see.” Davey’s expression was unreadable.

An awkward silence permeated the room. After a few moments, Race took Spot by the arm. “We’ll, uh. We’ll be going now. See you later, Jacky-boy.” With that, they headed to the secret passageway behind the bar, descended the stairs, and left for the warm, starless night.

“Why don’t I, uh. Take care of that for you,” Jack said, gesturing to the stack of crates. “There’s a wet rag on the bar if you could take a moment to mop that up.”

Davey obliged, setting to work on the spill. Jack was uncomfortable leaving him fully unsupervised, but he figured that Davey had no intent of violence against him. Or, at least, he hoped. 

Jack hummed to himself, now on edge in the silence, as he carried the rest of the crates down to the cellar. Miss Medda tended towards the standards, so Jack had hundreds of them memorized at this point. She’d practically raised him, and the walls and floors were rather thin in the building, so he’d grown up with her singing him to sleep in the club below. As he got older, he’d sing along to himself while she performed. But once Prohibition had hit, Jack had had no time for dreams. It was hard enough keeping himself and Miss Medda afloat as it was. He knew she had dreams of Broadway, and he hoped that, eventually, the speakeasy could keep her comfortable enough that that aspiration became a reality. Having set all the crates in their proper places, Jack set back up the stairs to send Davey off, still humming to himself.

Jack saw him hesitate, silhouetted in artificial lamplight. “That’s a nice tune,” Davey said. “See you around.” He lithely climbed the stairs out, shutting and locking the door behind him. Jack heard the lumber truck’s engine rev and breathed a sigh as the evening’s tension dissipated. 

Jack set to double checking Miss Medda’s work. Satisfied and exhausted, he double checked all the locks and headed upstairs to his apartment.

Miss Medda caught him in the hallway. “Why’re you still awake, boy?”

Jack groaned. He hadn’t expected to be caught. “Business,” he mumbled. “Can’t talk much about it.”

She nodded, understanding. “You can’t take a night off, can you?”

Jack shrugged noncommittally.

“Anyway, I had a favor to ask.”

Jack perked up.

“My voice is getting a little tired from singing all the time. I know you’re good, and you could use a break from that bar.” She put a hand up to keep him from talking. “Mush and Specs can take over for you while you open for me. Besides, I know your heart’s in performing.”

Jack didn’t know what to say. He couldn’t turn Miss Medda down. But how would he keep seeing Davey?

* * *

Jack was sweating.

He didn’t want to be sweating. That would look terrible onstage. Pit stains were the bane of every performer’s existence, apparently. His nerves were consuming him as he straightened his white bowtie and took in his appearance in the mirror. Were he not Black, he would fit right in with his clientele. It was a shame he couldn’t sit and watch Miss Medda from the audience after his performance—seats in the club were reserved for white patrons only. Jack didn’t like it, but it kept the business afloat and out of trouble, as well as in Rothstein’s favor. He couldn’t afford to lose that.

Someone knocked at the door of his tiny dressing room.

“Come in!” Jack called, eager to not be left alone with his thoughts.

In came Charlie Morris,  _ Miss Medda’s _ resident pianist. “How’re you doing, man?” he asked, easing himself into the other chair in the room and leaning his cane against it. “Ready for your first set?”

Jack laughed, hoping his panic didn’t show through too much. “Don’t know how ready I can be,” he said. He’d seen Charlie around the club for a while, since a piano was a fairly essential part of a jazz band, but Jack’d never gotten the chance to talk beyond serving him a drink after hours on occasion. He seemed to be a genial guy, so Jack figured he’d give good advice. “You got any tips?”

Charlie grinned. “Since this is your first night, I’d stick to some of our house standards. Your jacket can hide the pit stains—I know you think they’ll be obvious, but they won’t. And keep it calm, cool, and collected. The audience is gonna go wild for you, don’t worry.”

“How do you know that?” Jack replied.

“Man, everyone in this place’s heard you sing from the bar, or backstage, or upstairs. You aren’t as good at hiding it as you think.”

Jack blushed and turned away. “Thanks, pal. Means a lot, especially coming from you.”

Charlie took his cane and started to get out of the chair. “Of course. Don’t forget that you’re on in five.”

Jack blanched, and Charlie took his leave, patting Jack on the shoulder. “You’ll be fine. Just relax.”

Jack decided that any additional preening wouldn’t be worth it at this point and flipped through the book of standards Miss Medda had given him. Picking out a few, he squared his shoulders and headed towards the stage. It was showtime.

As he marched himself towards the stage, the ambient sound of the club built up to a dull roar. The tension in his shoulders decreased. This was just like bartending. Except this time, the barrier between himself and his patrons was an elevated stage, and the only product he had to deliver was himself. He hoped that’d be enough for them.

Collecting himself, he strolled out onto the tiny stage and waved, his trademark Customer Service Grin plastered across his face. “Hello everybody!”

The audience cheered, then quieted.

“You, uh. You may know me as Jack, your bartender here. But tonight, Miss Medda herself asked me to do her a little favor. So, here I am. Jack the Singing Bartender. Does that have a ring to it? I’m not sure, to be honest.” The crowd laughed, and Jack relaxed a little more. He could do this. “That’ll have to be good enough for now, I suppose. Hit it, Charlie!”

Charlie began to pound the keys, and the strains of a familiar tune came out. Jack took a deep breath, opened his mouth, and began to sing.

* * *

Half an hour went by fast, apparently. Jack wrapped up the end of his closing crooner (“Smart choice,” Charlie had complimented when going over the set list. “Making ‘em fall in love with you.”) and waved to the audience.

“Thank you all! I had a great time tonight. Uh, I’ll be over at the bar for the rest of the night. Thanks to Mush and Specs for keeping things in order while I’m up here.” Something thumped to the floor in front of Jack. He resolved to pick it up once he finished his spiel. “See you all tomorrow night! And enjoy the real star of the show—Miss Medda!”

Jack looked down. It was a rose. He quickly grabbed it as he cleared the way for Miss Medda, sparkling and shining like the star he knew her to be.

“Is it good to see me or what?” she said, smirking cheekily. The crowd cheered, and Jack scampered offstage.

Inspecting the rose more carefully, he saw a small note tied to it with initials and an address.  _ K. P. _ Interesting. He shrugged, grabbed an empty bottle from backstage, filled it up with some water, and placed the rose in it. Setting it on the small table in his dressing room, he changed ties and exchanged his jacket for a vest (a white bowtie would get messy very quickly while bartending), then slipped out to the bar.

“Thanks for covering me, boys,” he said, smiling at Mush and Specs.

“It was no problem,” Mush replied. “This guy might need to get his eyes checked, though.” He elbowed Specs jovially.

Specs pointed at the glasses on his nose. “I have these for a reason, you lollygagger!”

Jack laughed. “Feel free to do some table service. I’ve got the bar covered.”

Mush and Specs nodded, throwing towels over their arms and setting out.

As soon as they’d left the bar, streams of customers began coming up to Jack, fawning over him and ordering drink after drink. He supposed he had been quite the spectacle as a bartender-turned-star himself. Jack let himself revel in his newfound mild celebrity, mixing new drinks for his favorite regulars and keeping a winning smile on his face. Bartending, he supposed, was a kind of performance in itself.

Finally, the rush died down. Patrons had returned to their seats, entranced by Miss Medda’s act. She knew how to command crowds better than anyone else. Jack slumped against the bar, suddenly exhausted by the evening’s events. He didn’t notice the footsteps of the tall, elegant young woman coming his way until it was almost too late. He straightened up, brushing imaginary crumbs off his shirt. 

“Great job up there,” she complimented in a low voice. “You’ve got something magical.”

“Thanks, miss,” he replied, careful not to misstep. There was something indescribable in her demeanor, and Jack couldn’t risk anything.

She leaned on the bar, her flapper dress glittering. “What’s good here?” she asked. “I’m new around these parts.”

Jack thought for a moment, trying to buy himself some time. “How about I make you something custom,” he finally offered. “But I’ll need to get to know you a little first.”

She smiled, razor-sharp. “Sure. What do you want to know?”

“What’s your name? I need a better title for a drink than Girl-I-Just-Met-At- _ Miss _ - _ Medda’s _ ,” he said. “And… how about you tell me about yourself. What do you do? Got yourself a man?” he winked. Jack knew this was a dangerous game to play.

“I’m Katherine Plumber,” she replied, sticking her hand out for a shake. “Local writer, at your service.”

Jack took her hand, kissing it gently. Flirtation always won him some points with customers as long as he could read them right. He looked up at her through his eyelashes, then straightened back up. “One Katherine Plumber, coming right up.”

Jack never turned his back on her, but he did put his eyes on the drink he was concocting. Katherine Plumber. What an interesting name. His first guess for a drink would be something fruity and floral, but there was too much edge to her for that alone. He needed something simple and beautiful yet razor sharp. Idea in mind, he got the whiskey. “You ready, miss?”

She chuckled darkly. “You can call me Kath if you’d like. And yes. Let’s see it.”

“Alright, Kath. Here goes.” Jack set a glass in front of her, then poured a shot of scotch into one of the two silver mugs in front of him and added a little sugar to it. Taking out his trusty cigarette lighter, he set it aflame, quickly pouring it from cup to cup before pouring it over the ice in her mug. He then capped the drink with the bottom of one of his mugs and pushed it towards her. “Enjoy.”

Kath looked at the drink, wide-eyed, then back at him. Overcoming her suspicion, she took a sip. “That’s wonderful,” she said, taking another sip. “Thank you.”

Jack grinned, pleased that his trick had worked. “Of course, miss.”

“You know,” she said, setting her mug down, “why don’t you come along with me to a party this weekend. Midnight. Sunday.”

Jack’s jaw went slack. Kath seemed like a woman of means, and he knew something lay below her surface. “Um, sure. Where?”

Kath laughed. “You’ll figure it out. Thanks for the drink.” She blew him a kiss with her red, red lips, turned on her heel, and left the club.

**Notes for the Chapter:**

> thank you for reading!! i'm so glad y'all are enjoying this fic, so i decided to repay y'all with a quick second update!  
> a couple notes on historical context:  
> 1) yes, that really is one way that bootleggers got alcohol around! i'm too lazy to use html to link things but if you search "bootlegging" on google the fake lumber truck comes up in images  
> 2) the cocktail jack makes for kath is based on jerry thomas's blue blazer cocktail! and alcohol was generally served in non-traditional glasses in speakeasies so it was harder for the cops to spot (hence kath's mug)  
> thanks again!! please please please leave a comment!  
> follow me on tumblr @landlessbud and RB [this post](https://landlessbud.tumblr.com/post/621857494037299200/the-substitute-iim-david-he-mumbled-eyes-on) if you're liking this fic!


	3. Chapter 3

**Summary for the Chapter:**

> Jack encounters several velvet couches and a brush with the stars.

Hours later, Jack was still stunned. He thought back through the evening. The singing, Charlie… Kath wouldn’t have had a hand in either of those.

Wait a minute. The rose. The initials.  _ K. P. _ There was an address on it. Of course. The minute the club closed, he threw his towel down. “Mush! Specs!” he called. The two raced up to the bar. “Can you take care of closing tonight?”

They assented, and Jack nearly ran back to his dressing room. He stumbled in, almost falling over his chair, and carefully plucked the rose out of its vase, avoiding the thorns. The address looked to be on the Lower East Side. Interesting. Jack didn’t venture out of Harlem frequently, and this would be quite a trek for him. He didn’t know what this Kath character would do if he didn’t show up, though, and he didn’t want to risk that.

Jack left his dressing room in search of Miss Medda, still clutching the rose. On his way to her (larger, nicer) dressing room, he happened upon Charlie and the rest of the band, still packing up from the night’s performance.

“Great job, man!” Charlie called from across the stage. His fellow bandmates echoed the sentiment, and Jack blushed, a little overwhelmed by the flattery.

“I’ll see you fellas tomorrow night, alright?” Jack said, waving. They toasted to him (having received their complimentary booze for the night) and he grinned genuinely. Giving the band a mock salute, he continued on his way.

Jack took a deep breath. He now stood before Medda’s door. He wasn’t used to asking anything of her—he felt it was too much of an imposition given how much she had supported him over the years. But, Jack reminded himself, she  _ had _ told him he needed a break, after all. She’d probably be overjoyed to hear that he was taking a night off to go to a party. 

Jack raised his fist to the closed door and gently knocked.

“Come in!” Medda said, muffled slightly by the door.

Jack opened it and stepped in.

“Jack, dear! What a wonderful surprise,” she continued, giving him a quick kiss on the cheek. “Take a seat. What can I do for you?”

Jack flopped (perhaps a little dramatically) onto her lush velvet couch. Trying to make himself comfortable and keep himself awake, he let out a small yawn and rubbed his eyes a little. “I… uh… well…”

Medda smiled benevolently. “Come on, spit it out.”

“Alright, alright.” Jack sat up a little straighter. “I’d like to ask you a favor.”

“I’m all ears.”

Jack wasn’t quite sure where to begin. “So… I met this girl at the bar tonight—”

“Jack Kelly, you better not be thinking of anything dishonorable.”

“Mama, I swear I’m not,” Jack pleaded. “She invited me to a party on Sunday, and I’m a little more worried about what’ll happen if I don’t go than if I do.” He paused. “So. I need to take Sunday off, if that’s alright.”

Medda mulled over the thought for a moment. “That should be fine. Some of our guests might miss you here,” she jokingly warned. “Seriously, though. Be careful out there. And have fun.”

“Will do, Miss,” Jack replied. “I’ll see you tomorrow—same time, same place.”

Jack could hear Medda’s belly laugh from down the hall as he left and headed upstairs. He needed to plan.

* * *

Jack was surprised that nearly a week could go by so quickly. Before he knew it, Sunday had arrived. The Lower East Side was a bit of a slog from Harlem given that the subway ran from below Central Park and the number of transfers he’d have to make. Luckily, he had plenty of time to spare since he didn’t have to worry about the speakeasy for the day.

He poked through his (somewhat meager) closet, searching for the ideal outfit for the party. He couldn’t be too flashy—calling too much attention to himself was dangerous—but he also wanted to ensure he fit in. Most of his wardrobe consisted of fancier clothing for his bartending. He’d recently started collecting some jackets just in case, though he rarely wore them when bartending. These days, they were useful for his performances.

After rifling through his clothes a little longer, Jack selected his midnight blue jacket, pairing it with black pants, a black vest, and a white shirt and bowtie. The blue was enough to stand out a little from what he assumed could be a sea of penguin-like men, but subtle enough to prevent him from standing out. Snapping on some silver cufflinks, Jack pulled on the jacket and prepared to set out for his personal Sunday night odyssey.

Jack popped down to the speakeasy to check in on the bar for the night (as he suspected, Mush and Specs had everything under control) and perhaps to obtain a little liquid courage. Downing the shot, he checked the clock. Eleven. He’d better get going.

Jack paid the fare (he could only afford to partake in so many illegal activities without getting caught) and hopped on the El. The long ride afforded him some time to think, and, of course, his mind went directly to Davey.

Jack  _ had _ to be missing something. He’d never seen Race lose his cool like that, and there was something suspicious about how quickly any sort of conflict had been resolved. Something wasn’t clicking.

Suddenly, Jack realized he’d reached the 57th Street stop. He got off and prepared to transfer to the subway, still lost in thought. Careful not to get in the way of too many pedestrians, Jack gently elbowed his way through the crowds. Descending the stairs, he paid the fare and waited for the next southbound train. He decided to people-watch to pass the time.

One smartly-dressed woman carried a tiny dog in a purse. A shoddily-dressed man hunched in a corner, counting pennies. A gaggle of young women giggled, probably on their way to a speakeasy uptown. And there was a group of men all in black, fedoras tipped so their faces were barely visible. One was visibly taller than the rest, with a striking profile he’d recognize anywhere—wait a minute. Why was Davey here?

Just then, Jack’s train screeched to a halt in front of him. After getting in, he searched desperately through the windows to see if he could catch another glimpse of the men. They seemed to have disappeared. Strange, the way those mobsters could do that. But why would Davey be in a subway station of all places? And with so many other men? Jack was almost jealous of all of them. Spending time in close quarters with Davey sounded like a dream. Of course, he still had to figure out whether Davey was interested in him at all.

Jack barely noticed the signs indicating he’d arrived at the Bowery stop until it was almost too late. After running out of the car, he took a couple deep breaths on the platform. Almost there. He took the note with the address out of his jacket pocket and looked at it again. Confident in his ability to navigate, he climbed the stairs and set out.

Jack knew the Lower East Side had a reputation for being the seedier part of town. A mixing pot of immigrants of various nationalities and ethnic groups had settled there, and it was a known hotbed of organized crime. Jack just hoped he’d make it home safely, though he knew he wasn’t the type anyone there would be looking for.

At last, he turned the corner and spotted his destination. The apartment building looked pristine in comparison to the buildings surrounding it. Odd. He double checked the address, looking for the apartment number. Everything looked right. Jack tentatively approached the front door and pressed the buzzer for the apartment.

After the longest thirty seconds of his life, Jack heard the door unlock. He opened it and began his long march up the stairs.

Once he reached the fifth (and final, thankfully) floor, Jack looked at the apartment doors in front of him. 5B. That was what he was looking for. Locating it as one of the two doors on this floor (Jack shuddered to think of the sheer size of this apartment. It had to be larger than the speakeasy), he turned to it and knocked.

“Coming!” He could hear a feminine voice behind the door. It didn’t sound like Kath, though.

The door opened, and a puff of smoke escaped. A young brunette, fashionably styled in a black flapper dress with silver trim, peeked out. “Oh! Hello. You must be Jack.” She smiled warmly and let him in to the apartment.

Jack couldn’t help pausing to take in the extravagance of the room. Patterned Art Deco wallpaper surrounded a hazy, vibrant parlor, complete with velvet sofas, classily dressed men and women, and a shiny baby grand piano. Gilded statues stood as centerpieces on low tables: a silent indicator that whoever owned this apartment was obscenely wealthy.

Jack now remembered the woman who let him in. “Pardon my distraction, miss. What might your name be?”

She laughed, a silver tinkling bell. “You can call me Sarah.”

Jack grinned. “Nice to meet you, Sarah. What brings you here tonight?”

Sarah put a hand to her mouth to conceal another laugh. “Kath didn’t tell you, did she?”

“Tell me what?”

“I live here, silly!” she answered, poking Jack in the side. “Did she do the dark and broody and mysterious broad for you?”

“Uh, I assume so.” Jack was stunned. The sheer opulence of this place seemed to try to consume him. 

“Don’t worry about her. Kath’s bark’s worse than her bite.” Sarah patted Jack on the shoulder at this. “Here, I’ll go get her. Think about what you’d like to drink.”

Jack wandered towards the piano. He had a suspicion he’d be asked to sing at some point, so he figured there was no harm in checking out his options. A phonograph piped out some canned jazz as Jack thought through his catalog.

Someone tapped him on the shoulder. Jack turned.

Kath, clad entirely in red, smirked. “Fancy seeing you here,” she said, taking a puff of her cigarette. “Mind joining my canary”—she gestured to Sarah—“for a few songs?”

Though she appeared less intimidating than she had in the speakeasy, Jack could see the same glint in her eyes. He knew better than to refuse. “Sure, though I can’t play the piano for shit.”

“That won’t be a problem,” Kath replied. “She’s been playing for her entire life.”

Sarah took Jack by the arm and tugged him towards the piano. “Please? I haven’t had a duet partner in so long. I used to make my brother do it, but now he works such odd hours that he can’t anymore.”

“Say no more,” Jack said, an easy smile spreading like butter across his face. “How about… this one.” He pointed at a song in Sarah’s book of standards, and she nodded, plopping down on the piano bench. 

Out of the corner of his eye, Jack spotted Kath pulling out a small notebook and pencil.

Sarah, oblivious, began playing.

“ _ You were everybody’s sweetheart not so long ago… _ ” Jack began, looking across the piano into Sarah’s eyes. As she picked up her end of the banterous song, he noted that they seemed to have unintentionally matched quite well. His suit complemented her detailed, dazzling dress like the open night sky backdropping thousands of pinprick stars. They looked good together. Moreover, they sounded good together. Jack was having the time of his life.

Jack and Sarah continued performing song after song, slowly attracting an audience. They switched between duets and solos, filling the time between with a snappy repartee that had the whole apartment shaking with laughter.

Soon, Jack was so exhausted he could barely stand. Most of the guests had either left or flopped drowsily onto one of the many sofas. Leaning on the piano, he turned to Sarah. “We should do this again sometime.”

Her tired smile beamed back at him. “I’d love to.”

Kath snapped her notebook shut, bringing Jack back down to Earth. “That was the cat’s pajamas, you two.”

Jack blushed at the compliment. “It was my pleasure. Thanks for inviting me.”

“You’ll come again, won’t you?” Sarah practically pleaded, eyes wide. “We so rarely have new guests at our parties.”

Jack looked to Kath.  _ Our _ parties? When Sarah had mentioned that she lived here, he assumed Kath had extended an invitation on her behalf. Was he missing something? Or was it not that unusual for two ostensibly unmarried young women to share a place of residence?

“What, you think this is some sort of one-time invitation?” Kath asked. “Same time, same place. We’d love to have you again.”

Jack didn’t want to commit to anything yet. “I’ll think about it.” He winked, grabbed his hat, and headed out for the night.

* * *

Jack woke up to someone pounding on his apartment door. Yawning and rubbing his eyes, he sat up in bed. “What?” he called blearily.

“Let me in! There’s something you have to see,” Charlie’s voice came muffled from the other side of the door.

Jack stretched and got out of bed, picking up the pants he had left on the floor the previous night and pulling them on quickly. He then jogged to the door, unlocking it. “What’s going on?”

“Read this,” Charlie replied curtly, shoving a newspaper into Jack’s hands.

Jack dutifully obeyed, opening the copy of the  _ New York World _ to the dog-eared page. The Society column? Why would Charlie care about that? Scanning it, he spotted an article circled in pencil. 

_ STARS ON THE RISE? JACK KELLY AND SARAH JACOBS SPARKLE IN DEBUT PERFORMANCE _

Jack was shocked. How could this appear in the paper so quickly? And who knew about their performance besides the few people at the party last night?

Wait a minute.

Jack looked at the byline.  _ K. Plumber _ . Of course. That’s what the notebook had been about. Local writer… she was a reporter. Had she said anything about the speakeasy? Panicking, Jack read through the article. He could feel Charlie’s eyes burning holes through him.

“Look, there’s nothing about the speakeasy,” Jack said, placating himself as much as Charlie. “But, uh. This is a lot.”

“No kidding.” Charlie leaned on his cane. “What are you going to do?”

Jack mulled over the thought. He wasn’t sure how he’d see Kath again for sure. Then again… “I guess I’ll have to go back next week.”

Charlie sighed. “Alright, I suppose. But be careful. There’s something funny about all this that I can’t quite figure out.”

Jack gave him a mock salute as he hobbled down the stairs. “I’ll see you tonight!”

That night, as Jack finished his set, he could sense an energy that hadn’t been there before. The news must have spread quickly— _ Miss Medda’s _ was far more packed than usual. He bowed several times to boisterous applause, then gave over the floor to Miss Medda.

After cleaning up and changing, he slid back into his usual place at the bar. Patron after patron came up to him, seemingly shocked to be in the presence of the one and only Jack Kelly from the  _ World _ . His Customer Service Grin was coming in handy tonight. He wasn’t sure whether he wanted to curse or kiss Kath for the attention. On the one hand, he’d never made so many drinks in one night. On the other, this was earning Medda (and himself) the cash they needed to stay afloat. Perhaps stardom wouldn’t be all that bad.

By Thursday of that week, Jack was starting to get exhausted. Mush and Specs were incredibly helpful at the bar, but all of the patrons insisted on ordering through him. Tonight, he’d planned to take off after his set and leave the bar to them to get some much-needed rest.

His blue suit had become his trademark: Kath’s glowing review had remarked on it, and the audience went wild for it. Apparently Kath had quite the following in the papers, so Jack had been wearing it every day.

Jack shook out the tension in his shoulders and rolled his head around to warm up. He shuffled through his music, looking for the perfect opener. Oh, yes. There was one song he hadn’t tried in front of an audience yet. An uptempo piece would be a good way to start off. And perhaps he found the pun in the title a little too fitting for his present situation, but the audience didn’t need to know that.

Charlie arrived before the show to pick up the music, smirking a little when he looked at the one on top. “You goofy for that girl you met last week?”

Jack scratched at the back of his neck. “Something like that.”

Charlie let out a full belly laugh. “Whatever you say, old boy. Remember: you’re on in ten.”

Jack nodded and returned to fiddling with his bowtie. He’d have his little private laugh, and the audience would be none the wiser. That was all. So why did he feel like something was off?

He dusted himself off one last time and got out of his chair. The show had to go on, he supposed. Jack didn’t know why the walk to the stage felt so long tonight. He got set backstage, sending a quick thumbs up to Charlie. Earlier in the week, they’d decided that the band would begin the vamp as Jack made his entrance. Charlie cued the music, and Jack waited two beats, then strolled on.

He began with his usual hello and welcome and gave a quick smirk. Jack let his gaze travel over the audience.

“ _ You’re the cream in my coffee; you’re the salt in my stew… _ ” he began. Just then, he looked out at the front row. 

There was Sarah, who must have decided to come see him perform that night. But beside her? David Jacobs. He’d thought that her last name in the article had sounded familiar, but figured it was some sort of fluke. Horrifyingly entranced, Jack could see the similarities between the two siblings.

Jack couldn’t let the audience see this, of course. So he continued, pretending that the man this song was intended for wasn’t in the audience. “ _ You will always be my necessity: I’d be lost without you. _ ”

**Notes for the Chapter:**

> thank y'all for reading!!!  
> all i've got are some notes on music choices!  
> i've finally been forced to Actually Choose Songs for them to sing, so:  
> the song jack and sarah duet is Nobody's Sweetheart Now by Aileen Stanley and Bill Murray (listen [here](https://youtu.be/SKyYVcSmNhw))  
> the song jack sings at the end is You're the Cream in My Coffee by Jack Hylton (listen [here](https://youtu.be/IqaNW6TwT0U))  
> give them both a listen!! they're very good  
> friendly reminder to follow me on tumblr @landlessbud and rb [this post](https://landlessbud.tumblr.com/post/621857494037299200/the-substitute-iim-david-he-mumbled-eyes-on) if you're liking this fic!


	4. Chapter 4

**Summary for the Chapter:**

> Jack has a rough day, and new revelations come to light.

“ _ My woman done me wrong, _ ” Jack sang, closing his set for the night. He’d felt a little off-kilter ever since he locked eyes with Davey early on. Of course, he didn’t let the audience see that. He needed a smoke. 

Jack did his routine closing speech, welcomed Miss Medda, and headed backstage to his dressing room. He looked at his reflection in the mirror. Good—looked like his panic hadn’t shown through. Years of bartending seemed to have honed his ability to keep cool. Jack hung up his jacket, took off his bowtie, and unbuttoned the top few buttons on his shirt. The crowds that had amassed to see him (which still blew his mind) kept the dark, cramped speakeasy hot and humid. Jack worried he’d sweat through his jacket one of these days.

Checking his pockets (yes, there was the pack of cigarettes and his lighter), Jack slipped out the back of the club. He lit a cigarette and lifted it to his lips, breathing in the smoke and night air. The tension eased out of his muscles as he leaned back against the brick wall and reveled in his relative isolation. 

Exhaling, Jack fell back into his thoughts. Why did Davey have to show up tonight of all nights? He never left Jack’s thoughts as it was, and his appearance at  _ Miss Medda’s _ simply made it worse. The only feasible reason Jack could think of was that Sarah dragged him here, not knowing that he already knew Jack. Sarah must be unaware of her brother’s career choices, though Jack did remember her remarking on his unusual working hours at the party. 

Footsteps thudded gently down the alley. There should not be footsteps thudding gently down the alley. Jack immediately went on alert, stubbing his cigarette out against the wall and checking his back pockets.

Foolishly, he’d left his pistol behind. Nothing could save him now. Jack sincerely hoped whoever was coming his way didn’t intend on hurting him. His white shirt stood out starkly against the wall, and he didn’t have enough time to get to the back door, unlock it, and go inside.

Jack looked up.

Down the alley, he could see a tall, slender masculine figure in a fedora and long coat despite the warm weather. Beside him walked a smaller figure, also in a long coat and hat. Could it be? Jack sincerely hoped his intuition was correct.

As the pair approached, Jack began calculating his options. Had he said something wrong about Rothstein recently? Or had his ascent to moderate stardom incited some hateful rage? He prayed to whatever deities he could think of that he’d make it out of this encounter alive.

The footsteps got louder. Whoever this pair was, they were getting a bit too close for comfort.

The smaller figure took off their hat. Sarah Jacobs stood before him, and Jack could not have been more relieved.

“Hello, Jack,” she gushed. “That performance was the duck’s quack. We should really come out here more often to see you!”

At this, she elbowed her companion and hissed something into his ear. Wordlessly, he removed his hat, revealing that it was in fact Davey beside her.

Jack squeaked out a greeting, though he’d deny it to anyone that asked.

“Jack, meet my brother David. He’s had to hear me blabber on about singing with you all week, so I figured I’d show him what I was talking about. David, this is Jack.”

So Sarah didn’t know about Davey’s mob involvement, nor his bootlegging. Interesting. Jack reached his hand out for a handshake. It hung in the air for a moment before Davey took it in his own, shaking with intent and some strength. “Nice to meet you, Jack.”

Jack risked a glance into Davey’s eyes. He could practically see  _ don’t tell her don’t tell her don’t tell her _ written across Davey’s face. “My pleasure, David,” he replied. He wasn’t sure if he was imagining the way Davey wilted briefly at being called David.

Sarah glanced at the two of them, somehow ignorant of the tension between them so thick it could be cut with a knife. 

“I’m trying to convince David here to come to the party this week, but he always says he’s too busy or too tired,” she said, rolling her eyes. “I thought you might be helpful with that.”

Jack knew why Davey was skipping the parties—he must be exhausted from his deliveries the night before. Then again, if he slept in, it shouldn’t be a problem. Did mobsters have day jobs? Perhaps Davey didn’t want to alter his sleep schedule too much if he did. Or maybe he made enough money from his mob work that he didn’t need a day job. Nevertheless, Jack let an easy grin spread across his face. “C’mon, Mac. I can show you how to have a good time if you show up.”

Was there a faint blush on Davey’s cheeks, or was it the reflection of the light from the apartment windows upstairs? Jack couldn’t be sure.

Davey sighed, clearly outmatched. “Guess I’ll have to find out somehow, since I seem to be Mr. Has No Fun.”

Jack and Sarah cheered quietly, never forgetting the precariousness of an alley conversation. 

“We’ll see you Sunday, Jack. Remember: same time, same place,” Sarah said, taking Davey by the arm. They both replaced their hats and began their walk out of the alley as Jack wished them a quick farewell.

He watched them leave. Though he desperately wanted to trust Davey, Jack knew too few of the secrets lurking behind those alluring hazel eyes of his.

Once he could no longer see Sarah and Davey, Jack pulled his keys out of his back pocket, unlocked the back door, and headed back inside. Intending on spending the rest of the evening in his dressing room, Jack slipped into the hallway behind the stage. Medda was still performing, so he made sure to tiptoe and close the door gently. He practically collapsed in his chair.

Leaning back, Jack allowed himself to relax briefly. He stretched, trying to work out more of the tension in his muscles. His back popped, and Jack sank back into the chair. He paused for a moment, limp, then sat back up, elbows on the small table in front of the mirror. Jack stared into his eyes in the mirror. If he listened carefully, he could faintly hear Medda wrapping up her set. He let her voice soothe him into a trance-like state, mind totally vacant. 

Jack only realized that Medda had finished her set when he could hear the raucous applause and cheering of the speakeasy crowd. He debated whether to get up and congratulate her for another well-done performance (she didn’t need to know he hadn’t really been listening) or simply to stay sitting. He was already so comfortable in his chair that he had nearly no inclination to get up, anyway.

A few minutes passed. Jack heard a gentle  _ rap-rap-rap _ on his door. “Come in!” he called, momentarily forgetting about the lack of floor space in his closet-sized dressing room.

Miss Medda herself peeked through the doorway. “Why don’t you come pay me a visit, Jack?” she said, beckoning him to her dressing room.

“Anything for you, Miss Medda,” Jack replied with a grin. He heaved himself out of his chair, buttoned his shirt back up, and set out. 

The door to Medda’s dressing room was open when he got there. Strangely, some of the miscellaneous paraphernalia she’d been amassing over her years as a performer at the club was missing. Jack gracelessly flopped onto her sofa.

“Wonderful performance tonight, Miss. It was certainly the bee’s knees,” Jack said. He wasn’t sure why she needed to talk to him so badly, so he figured opening with a compliment was never a bad idea.

Medda smiled warmly. “Thank you kindly.” She paused, seemingly trying to figure out how to phrase her next statement. “You may be wondering why I asked to talk to you tonight.”

“I love you dearly,” Jack began, hoping to score some points, “but I will say I’ve never been called in here like a schoolboy to the principal’s office before.”

She laughed, clear and true. “That… may be true. I do need to talk to you about something important, though.”

Jack sobered up. Medda rarely spoke in terms like these.

“I… well, Jack, I haven’t been completely honest with you,” she began.

Jack blanched.

“Remember when I asked you to open for me? That… wasn’t only because my voice was getting a little tired. I was at an audition.”

Jack was shocked. He knew Miss Medda had eventually planned on going legit, but he hadn’t realized how soon that would be.

“Long story short, I got the part, and rehearsals begin next week.” 

Jack’s eyes went wide. “So that means—”

“Yes, Jack. Unfortunately, I will no longer be able to perform here. But I’ll still be here, don’t worry,” she placated him. “I just won’t be on that stage anymore.”

“If you’re going, then—”

“Yes, Jack. I need a replacement. And I firmly believe that you’re the man for the job.”

Jack’s voice went up several octaves. “Me?”

Medda shook her head, laughing to herself. “Yes, you. You’ve been opening for me long enough that you’ve got it down, and, thanks to that reporter, you’ve gotten yourself quite a following.”

Jack opened his mouth to speak, but Medda cut him off.

“Mush and Specs can handle the business side, Jack. They’ve been covering for you for a while now. All you need to worry about is keeping your voice healthy and looking pretty, neither of which should be particularly difficult for you,” she concluded.

Jack wasn’t sure whether to be insulted or honored. He decided on a healthy mixture of both. “Mama,” he whined dramatically.

“You’ll be great, dear. I know it,” Medda said, consoling his anxieties.

“Thank you, Miss,” Jack replied. He patted the sofa absentmindedly.

“Oh, yes. I forgot to mention this. This dressing room will be yours, too. You’ll start Monday, so I’ll have all my things out before that evening.”

Jack took in the space. He’d actually have elbow room here—and he could entertain guests, should he so choose. He very intentionally did not think about whom those guests would be.

“Thank you,” Jack repeated. “I—it’s been a long day, so I’m going to turn in for the night. This all means a lot.”

Medda smiled gently. “Get some rest, son. You’ve got a big week ahead of you.”

Jack kissed her on the cheek and left her (soon to be his!) dressing room. He popped by his own to pick up the various accoutrements and clothing items he’d left behind earlier, then plodded up too many stairs and practically fell into his bed.

* * *

Jack hesitated at the buzzer to Kath and Sarah’s apartment building. How was he going to break the news to them that he couldn’t return to their parties for the time being? Perhaps he’d do it at the end of his set and invite his fellow guests to come to  _ Miss Medda’s _ to see him perform. Yes. That’d do.

He pressed the buzzer and took a deep breath. The door unlocked, and he began his five-story climb.

Upon reaching the top, he took another deep breath at the door. Jack knocked gently.

Almost immediately, the door opened. Kath smiled, sultry. “Welcome back. Come on in.” She gestured inside, and Jack stepped in. That smoky haze once again consumed him as he made his way to the piano.

Kath walked with him, occasionally taking a puff off of her elegant cigarette. She was radiant tonight, glittering in a golden dress. Jack’s eyes were constantly drawn to her—the bright central star that everyone else orbited in the galaxy of the party. “What’ve you got up your sleeve tonight?” she asked casually.

“I’m not sure yet,” Jack replied. “Guess it’ll depend on what Sarah feels like doing tonight.”

Kath waggled her eyebrows suggestively, and Jack groaned. “You know that’s not what I meant.”

“Sure,” she said.

Suddenly, another arm looped through Jack’s elbow.

“Jack!” Sarah exclaimed. “I was wondering when you were going to show! Come, come.” She steered him to the piano.

“What’s on the docket tonight, Miss Canary?” Jack asked, leaning on the piano.

Sarah flipped through her sheet music for a moment. “How about… this one?” she said, pointing at the open page.

Luckily, Jack had learned this particular song from hearing Miss Medda perform it thousands of times with various duet partners. “Let’s do it.”

Sarah began plunking out the introduction to the song, and, out of the corner of his eye, Jack saw Kath gathering a crowd. “ _ You’ve got to listen to your sweet mama, _ ” she sang.

Jack fell into the music, forgetting that anyone besides Sarah was in the room. A few songs later, he got a short break while she performed a solo piece. He took advantage of the opportunity to inspect his audience. As he scanned the room, he spotted a familiar figure beside none other than Kath herself. Davey. So he had decided to come after all.

Kath and Davey, oddly enough, seemed caught up in their own world. While Jack watched, curious, Kath slung her right arm around Davey’s shoulders, smiling. The contrast between her arm and Davey’s simple suit allowed Jack to see something sparkling on her hand. Was that—oh, no. Davey kissed Kath’s cheek. Jack, too, could connect dots. He couldn’t bear to watch any longer.

That was almost certainly an engagement ring on Kath’s finger. He hadn’t caught it before because Kath herself was sparkling so much. But why would she be engaged to Davey, of all people? Davey hadn’t mentioned anything indicating he even knew her. In fact, Jack had thought that Kath was romantically involved with Davey’s  _ sister _ . Something had to be wrong. There was no other answer.

Sarah snapped her fingers at him. “Jack!” she hissed quietly. “You’re up!”

Jack brought himself back to reality as Sarah cued him into an old, familiar standard. This was the worst time to be distracted, especially as one of very few Black people in the room. His continued acceptance by the mostly-white crowd was predicated on his capability as a performer. Jack didn’t let any of his anxiety show through, instead projecting a charming, worry-free image. After all, he couldn’t afford to compromise his career with a little thing like love.

If Jack happened to let an undercurrent of melancholy fill the rest of the set, that was his business. As Sarah wrapped up their final song, letting the last few notes float away into the night air, Jack turned to the audience.

“Thank you all for having me here, especially Kath and Sarah,” he began.

The crowd cheered for their hostesses. Jack allowed himself a moment to enjoy the energy of the room, especially since this most likely would be his last time here ever.

He let the bittersweet feeling consume him as the applause died down. “I, well. You all may know that this isn’t the only place I perform.” He got a couple more cheers and an eye roll from Kath. “Yeah, yeah, I know. Sounds like the beginning of a great marketing pitch. However, I’ve just been the opener there for the lovely Miss Medda herself.”

The crowd whooped and hollered—she was a big name in entertainment, after all. 

“She’s been so good to me, but now she’s moving on. I don’t know if I’m allowed to let you in on all the details yet, but you all can keep a secret, right?” Jack slipped easily back into his Customer Service Persona. “Soon, you’ll be able to find her on none other than the Great White Way. Maybe it’s not  _ as _ white anymore.” Jack knew the joke was a risk, but knowing Kath and Sarah, he figured he could get away with it. “Needless to say, she won’t be performing at her club,  _ Miss Medda’s _ , anymore. But I’m not going anywhere—she’s left me with some big shoes to fill.”

Jack risked a glance at Davey. His eyes were wide. What was so shocking about not being in on information like that? There was no way Davey could know  _ everything _ about the operations of the club. Jack couldn’t keep falling down this rabbit hole.

“That’s right, folks. Starting tomorrow, you can catch little old me as the headliner at  _ Miss Medda’s _ all the way up in Harlem.”

“But—” Sarah attempted to interject.

“Yes, this is unfortunately another case of good news and bad news. The bad news is that… well. You all have been witness to my final performance outside  _ Miss Medda’s _ for the time being. I couldn’t thank you enough for that,” he continued, avoiding eye contact with Kath by looking at her ear. “I’ll miss being here and singing with this lovely songbird”—he gestured to Sarah—“but I’m fairly certain this is a see you later, not a goodbye.”

Speech done, Jack prepared to leave. He didn’t want to be anywhere near Kath and Davey right now. Pulling his jacket back on and checking his pockets, he quickly angled for the door.

Jack could hear Kath and Sarah calling for him as he shut the door behind him, but he continued on, barrelling down the stairs. The faster he could put distance between himself and what had become his waking nightmare, the better.

He’d thought he could trust Davey. Moreover, he’d thought he might have a chance with him. Something was wrong. Davey was still too low-ranking in the mob to have any hopes of an arranged match.

Or was he?

Jack thought out the previous few weeks. There’d been the strange interaction with Spot and Race, Davey at the subway… and Jack had no idea how Kath and Sarah could have possibly become so wealthy as to have an apartment like theirs, especially since Sarah was clearly Davey’s sister.

But how did this explain Mayer’s serving as his runner for so long?

Perhaps Kath was simply wealthy enough to finance this lifestyle for herself and Sarah. Sarah would’ve been encouraged to move in—one less mouth to feed is one less mouth to feed, after all. Through Sarah, Kath must’ve met Davey. That sounded much more likely. Why would Davey lie about the mob to Jack?

It didn’t make the engagement hurt any less. Every time he thought about it, it was another punch to his gut. Jack felt sick.

Footsteps thudded behind him. Someone was running.

“Jack!” Davey called. Great. Exactly what he needed.

Jack kept walking, increasing his pace marginally.

Davey, with his stupid long legs and gentle face and dark hair, grabbed Jack’s elbow. “Jack. Please. We should talk.”

Jack attempted to extract himself, but Davey held on firmly. “What is there to talk about? I have eyes.”

“Please, Jack.” Davey had gone into full doe-eye mode. Jack was a goner.

Jack shook his head and looked away.

“I swear it’s not what it looks like,” Davey pleaded.

“I don’t see how that’s possible,” Jack retorted, finally freeing his arm. “Thanks for coming. Goodnight.”

Jack didn’t turn back. He ran to the nearest subway station and got himself aboard the first train there. As the train pulled away, he caught sight of a familiar figure running down the stairs. He smiled to himself. Davey was too late.

**Notes for the Chapter:**

> thank you all so so much for reading and enjoying!!
> 
> some notes on the songs:  
> the first song Jack sings is My Woman Done Me Wrong by Clarence Williams featuring James P. Johnson (listen [here](https://youtu.be/39O9MBno40M))  
> the song Jack and Sarah duet is You May Be Fast But You Won't Last by Aileen Stanley and Billy Murray (listen [here](https://youtu.be/YOyJG6vZb-M))
> 
> please leave a comment! and don't forget to follow me on tumblr @landlessbud and rb [this post](https://landlessbud.tumblr.com/post/621857494037299200/the-substitute-iim-david-he-mumbled-eyes-on) if you're liking this fic!


	5. Chapter 5

**Summary for the Chapter:**

> Jack just can't seem to relax.

Jack settled back into his new dressing room chair, loosening his bowtie and unbuttoning the top of his shirt. He took a deep breath. Four days into taking over for Miss Medda, he knew there was still plenty of room in the big shoes he was filling. This was the first moment since he’d started the new gig that he felt he could truly relax. Thursday nights began the weekend rush, but, now that he didn’t have to bartend, Jack enjoyed them much more. Yes, it wasn’t silent—the muffled noise of the speakeasy reached his dressing room, the band’s horns and piano blending with the chatter of patrons, all there to see Jack.

He’d recognized a few faces in the audience from the party on Sunday. There seemed to be more people he’d seen at that party coming to  _ Miss Medda’s _ each night. Luckily, Davey had yet to show. Kath and Sarah hadn’t either. Good. Any of their presences would’ve thrown him off his game—replacing Miss Medda was hard enough as it was, though the audience didn’t seem to care that much.

Someone flung the door open.

Jack grabbed his gun off the table and immediately pointed it at the intruder.

Spot and Race paused in the doorway.

“We’d greatly appreciate it if you’d be so kind as to aim that bean-shooter somewhere else, Jackie,” Spot said, calm and collected, the threat implicit.

Jack lowered the pistol slowly, never taking his eyes off them. Setting it back on his expansive makeup table, he painted a calculated grin on his face. “Welcome in, boys. Take a seat.” He motioned to the velvet sofa Miss Medda had so kindly left behind for him.

Spot quickly closed the door behind him, then took a seat beside Race.

Someone else knocked on the door.

“WHAT?” Jack yelled, disgruntled.

Specs opened the door and peeked in. “You have visitors.”

Jack rolled his eyes. “Don’t you think I know that?” he replied, pointing at Spot and Race.

Specs blushed, mock-saluted the group, shut the door behind him, and returned to the bar.

Jack turned back slowly, pulling at the tension like it was taffy. He crossed his right leg over his left and placed his hands on his knee, apprehensive.

After fidgeting briefly, Race was the first to break the silence. “Jack, you can’t keep doing this.”

Jack was confused. “What?”

Race gestured to the general atmosphere around him. “This. Y’know. Getting on that stage.”

“ _ What? _ ” Jack asked, shocked and offended.

“Look, pal,” Spot began in a low tone. “We normally like to stay out of your business, since you stay out of ours. But I don’t like seeing too many familiar faces here. Besides yours, of course.”

Jack could not figure out for the life of him what Spot and Race were going on about. He furrowed his brow quizzically.

“What we’re saying,” Race attempted to clarify, “is that people we may be  _ familiar _ with are people that you should  _ not _ be familiar with. So, when people we  _ are _ familiar with start showing up in droves for no apparent reason, we get…”

“Concerned.” Spot completed the sentence.

Jack raised an eyebrow.

“He may not show it, but Spot  _ does _ have a heart,” Race interjected.

Jack had assumed so, considering the rings, but he’d never been quite sure whether there was any love for him in it. But what kind of people would get Spot and Race worked up enough to try to warn him?

Jack, of course, couldn’t possibly show how touching this comment was. “Sure.”

Spot grumbled something under his breath, and Race leaned back with a laugh. Jack didn’t understand what was happening.

Spot and Race turned back to face Jack wearing matching stony expressions.

“Look, fellas,” Jack continued, “I’ve got no idea who or what you’re yapping on about.”

Spot cleared his throat. “Your new audience members. I haven’t seen them around these parts before.”

“Oh!” Jack finally understood. “Yeah, I sang for them at Kath and Sarah’s parties and mentioned that I also sing here.”

An indiscernible look passed between the two mobsters. “Kath and Sarah, you say?” Race echoed.

“Yeah. Kath came in here one night and invited me. What’s so wrong about that?”

Spot, though he was shorter and squatter than him, pulled Race up by the elbow. “We’ll be going. It’s been a nice chat.”

“What—I still don’t understand!” Jack exclaimed.

Race turned back at the door. “You’d better ask your runner.”

The door slammed shut behind them, and Jack was once again alone in his dressing room.

* * *

Over the course of the week, Jack had taken to spending evenings in his dressing room after his performances. He’d finally gotten a chance to decorate, and now it felt like a cozy second home, especially since it was nearly the same size as his apartment. He’d take the time to relax and decompress while waiting for the patrons to leave. The staff had a nightly drink together, but they weren’t allowed in the seating area until they closed for the night.

He’d decided to move Medda’s old grandfather clock to his dressing room. Its presence comforted him in a way he didn’t quite expect. Jack hadn’t seen her since he started headlining: their schedules kept them on practically opposite hours. The clock anchored him, reminding him that, even if he couldn’t see her, Medda would always be there for him.

A gentle  _ tap-tap-tap _ at his door interrupted Jack’s thoughts.

“Come in!” he called.

Mush popped his head in. “I, uh, was grabbing tonight’s delivery, and…”

“What about it?” Jack started. Something could be wrong. He’d been on edge ever since Spot and Race had dropped by.

“Don’t worry. I don’t think it’s anything particularly bad,” Mush said, pulling an envelope out from behind his back. “But this came in with it. It’s addressed to you. Figured you wouldn’t want us crowding around you while you read it. We’ll be at the bar when you’re ready.”

Jack took the envelope, suspicious, as Mush headed back to the bar. He flipped it over.  _ To Jack _ , the loose but beautiful cursive read.

There was only one person this could have come from.

Jack’s more masochistic tendencies encouraged him to open the envelope, revealing a letter inside. Gently setting the envelope on the makeup table behind him, he unfolded the letter.

_ Dear Jack, _

_ I’m afraid I wasn’t able to fully explain myself last weekend. I can’t say much more, but please meet me at next week’s delivery. _

_ Mouth _

Jack had to laugh. What more was there to explain? He’d gotten the picture. It was a nice try, but there was no way he would meet Davey.

He wasn’t sure what to do with the letter, though. Leaving it in his dressing room was too unsafe—the door didn’t lock, and so many people were in and out that it was easy for papers like this to get lost. He’d have to take it to his apartment and figure out a secure place there. Perhaps a dresser drawer or under his mattress would do. For now, he tucked it in his back pocket and headed to the bar for a drink.

Mush, bless his heart, had already prepared Jack’s I’m-Having-A-Rough-Day drink: a straight shot of whiskey, to be followed with another (and perhaps more, depending on the roughness of the day). Jack took the empty seat at the bar, then downed the shot.

“Bad day?” Charlie asked, nursing his mug.

Jack shrugged. “Something like that.”

“Anything we can do to help?” Buttons, one-half of Jack’s new opener, said.

Jack shrugged again mutely. He appreciated her care, but she’d barely been performing there for a week. He wasn’t sure he was ready for everyone at the speakeasy to know his intimate business, particularly when it came to ties to the mob.

Buttons and her—companion? friend? lover? Jack wasn’t quite sure—Smalls had caught Jack’s attention as buskers a few streets over from the club. Their comedy act had caught his attention, and, when he learned they could sing, he insisted upon giving them the opening act slot at  _ Miss Medda’s _ . They had a skill and presence that Jack could only dream of, and they could get audiences warmed up like nobody’s business. After Miss Medda, of course, they were quickly becoming his two favorite performers.

Smalls sidled up to him. “You should’ve seen the looks on their faces tonight when we did the Miser’s Dream. They went completely goofy when I kept pulling coins out of the piano,” she enthused.

“Sorry I missed it,” Jack replied candidly. His apology was genuine—there was, unfortunately, no way for him to watch their performance because he wasn’t allowed in the seating area of the club during business hours. “Tell me more.”

Smalls launched into an enthusiastic description of their entire act that night as Jack sipped at his whiskey and listened.

* * *

Jack laid on his bed, trying to ignore the anxiety creeping up his throat.

Davey would be in the alley, waiting for him, in minutes. Jack had no intention of being there. Sleep wasn’t coming. He prayed silently that nothing would come of his missing the meeting. His blinds were shut tight and all lights were off, so he wouldn’t be visible to Davey.

He could just barely hear the truck trundling into the alley. Its brakes squealed as it came to a stop. Jack caught a cavalier door slam, then silence hung in the air.

That was definitely the sound of a gun firing, followed by a shout. Was that Spot? But what would he be doing here on a delivery night?

Jack had to see what was happening. He crept out of bed to his windows, peeking out from under the blinds.

There was Davey, pointing what had to be a pistol at Race, who seemed to have just emerged from the shadows. Spot had stepped out from the opposite corner. Jack was too far away to see every detail, but it looked like there was blood trickling down the side of his face. Both Spot and Race held their hands in the air.

Wait a minute. Davey’s mouth was moving. Jack had never cursed his fourth floor apartment more than this very minute. He wished he could see Spot and Race’s faces. Davey looked more imposing than Jack had ever seen him. His face was stony, but his manner was cool and collected. The pistol looked like a seamless extension of his arm.

A distant movement caught Jack’s eye. The driver’s side door of the truck inched open. A slight, small figure stepped out, quickly pulling out another pistol with a trained hand. The figure looked oddly feminine for someone involved with mob business. Weren’t all mobsters men?

Apparently not—Jack could now clearly see that that was Sarah Jacobs in his alley. Had she been Davey’s driver this entire time? She had seemed so bubbly and sweet at the parties that it was difficult to remember that this indeed was the same woman. All control and poise, Sarah stalked down the alley, still unnoticed by the three men.

Soon, she stood beside Davey, gun trained on Spot. Jack could just make out her mouth moving. There was an unfamiliar fierceness in her expression. Jack was terrified.

Was everything he knew about Sarah a lie?

Jack watched in horror. Sarah and Davey forced Spot and Race to separate and leave down opposite sides of the alley, never dropping their guns. As soon as Spot and Race had vacated the premises, Sarah hopped back into the driver’s seat of the truck, and Davey continued the delivery as if nothing had happened.

Was Jack imagining things, or did Davey glance up at his window?

The truck lumbered off into the night. Jack, finally exhausted, fell into bed.

* * *

The following Friday, Jack smoothed the lapels of his green velvet suit. He felt somewhat outclassed for Miss Medda’s opening night, but he reminded himself that she’d gone to all the trouble of securing him a free ticket and practically raising him, so he should be there. Smalls and Buttons could handle taking over for one night.

He remembered the New Colonial Theatre from the vaudeville shows Medda had taken him to as a boy—clowns, dancers, magicians, strongmen, actors, and musicians. The music bug had bitten him early, and Medda had certainly done nothing to keep him from it. These days, the New Colonial featured more musical revues starring Black performers. Medda had urged him to go see a couple on occasion, but he never took a night off. This, he supposed, was his chance to see what she was talking about.

He approached the usher, who handed him a playbill and took his ticket. “Third row from the front, five seats in,” he said, pointing in the direction of Jack’s seat.

Jack thanked him, stunned that Medda had secured him such a good spot. After all she’d done for him, she still gave him more than he deserved.

He took his seat. He’d intentionally come early so he could make sure he didn’t miss anything. It wasn’t every day Miss Medda opened on Broadway, after all. 

Jack took a moment to drink in his surroundings. Theatres were quickly becoming some of his favorite places: the elaborate, gilded decoration combined with the collective anticipation of something wonderful filled his heart with an indescribable joy. He took a deep breath, trying to let the feeling consume him.

What show was this, again? He hadn’t gotten a chance to actually speak with Miss Medda since she’d gotten the job—she’d slipped the ticket under his door last week with a note. He checked his playbill.  _ The Chocolate Dandies _ , it read. Interesting. Jack had no idea what to expect. He flipped through the pages, searching for Medda’s bio. There it was.  _ Medda Larkin _ . She’d listed some of her solo performances and work in little theatres uptown, but obviously had censored her affiliation with the speakeasy. And—the last line.  _ To Jack: all the world’s a stage. Find yours. _

Jack had to brush away the tears welling in his eyes. He didn’t deserve Miss Medda’s kindness, yet she kept giving it to him.

The orchestra began to play. Jack started, turning his eyes to the stage, as the lights went down.

The first act had captivated Jack. He’d never seen a musical that brought real horses on stage before, and Medda had been side-splittingly funny in her role. He hoped that the horse owner would never have to wake up from his dream.

Jack didn’t feel like walking around, so he stood up and turned around to look at the back of the theatre. He had no idea how it could get more magnificent each time he looked.

A well-dressed trio caught his attention: two young white women in fashionable, drop-waist dresses, and a man, still wearing a hat indoors, in a silver suit. He paused. The three turned around, and he was looking at none other than Kath, Davey, and Sarah. At least Kath wasn’t hanging off of Davey’s arm tonight. In fact, Sarah seemed to be hanging off of Kath’s.

Sarah’s demeanor held none of the steeliness of the previous Saturday night. As Jack watched, she threw her head back, laughing at something Davey had said. Something uncomfortable bubbled in Jack’s stomach. He wasn’t sure if he wanted to punch Davey or ignore him for eternity or—

Jack wouldn’t let himself complete that thought. Davey had betrayed him by getting entangled with Kath. Then again… why was Sarah between Kath and Davey?

He was so lost in his thoughts that he didn’t catch the three of them approaching. Conveniently, however, the lights blinked, signaling the end of intermission. The orchestra began the entr’acte, and Jack sat down. He was a bit antsy until the curtain opened, but then he lost himself in the world of the show once more.

After the cast bowed, Jack remembered the note Miss Medda had left:  _ Wait in the lobby after. I’ll come get you. _ He let his fellow audience members filter out of the theatre, drinking in the opulence. There was nothing quite like an empty theatre. He enjoyed a tamped-down version of the feeling in  _ Miss Medda’s _ after hours, but a big Broadway house was on another level. The weight of the knowledge that, just minutes ago, this space had held so much life and heart settled on Jack’s shoulders, and, fulfilled, he got up and headed to the lobby.

He selected an out-of-the-way bench to do his waiting. Medda had worn several elaborate costumes and a fairly significant amount of makeup, so he figured it might be a while before she showed up. Surprisingly, Jack only had to wait for a couple of minutes.

Medda came through a slightly hidden doorway. “Come here, son,” she beckoned, enveloping him in a warm hug. “How’d you like the show?”

Jack gushed on the walk to her dressing room. He’d been astounded not only by her performance but also the sets, sound, lights, costumes… everything had blown his mind.

She opened her dressing room door, letting Jack in behind her.

She’d decorated it to look almost exactly the same as her dressing room back at the club. Jack felt tears coming to his eyes for the second time that night. Even far from Harlem, Medda knew how to make anywhere feel like home.

**Notes for the Chapter:**

> thank you all so much for reading!!  
> so sorry this chapter was a little later than i thought it would be, but also i am beholden to no update schedule so you really can't get mad at me.  
> there is SO MUCH fun historical context to this chapter!!  
> first off! yes, it is true that speakeasies in Harlem would have white customers, which relegated Black people to being staff/performers only. this segregation existed throughout prohibition and it's really terrible but i felt it was important to acknowledge it in this fic.  
> since i had to google this, yes, blinds did exist in the 1920s  
>  _The Chocolate Dandies_ is a real musical from 1924! you can read more about it [here](https://blackworkbroadway.com/The-Chocolate-Dandies-1924), and one of the photos i posted in my contextless spoilers post is a production photo!  
> this musical did indeed play in the New Colonial Theatre, which was a theatre in the (former) San Juan Hill neighborhood in the Upper West Side. unfortunately it's really hard to find pictures of it online bc it was torn down in the late 70s, but i based the description loosely off of other bway theaters i've seen.  
> thank you again for reading!!  
> i'm @landlessbud on tumblr - please like/rb [this post](https://landlessbud.tumblr.com/post/621857494037299200/the-substitute-iim-david-he-mumbled-eyes-on) if you're enjoying this fic! (and feel free to shoot me asks about it - you never know what secrets i might spill!!)


	6. Chapter 6

**Summary for the Chapter:**

> Jack makes some discoveries.

“My God,” Jack sighed dramatically. “You certainly know how to make a man feel at home.”

Medda laughed, swatting him gently on the shoulder. “Stop it, you.”

“Seriously, Miss. I can’t believe you picked up your dressing room at the club and transported it right here,” Jack said innocently.

“Jack Kelly, you will be the death of me,” she replied with a chuckle. “Come, sit.” Medda gestured to a new couch, somewhat similar to the one she’d let Jack keep in his dressing room. 

Jack obeyed, taking a minute to actually marvel at his surroundings. This was a real Broadway dressing room. And it was _Medda’s_. Witnessing her dream coming true made Jack feel like he was in a fairy tale. His brain momentarily stopped functioning, and he poked at the sofa. “It’s real soft.”

Medda smiled gently. “Of course it is. That’s how you like it. Don’t go thinking I’ve forgotten everything about you since going legit.”

Jack’s happy tears were not going to go away tonight, then. She took a seat beside him, wrapping her warm arms around him. Jack felt small again: like the boy he was when Medda took him in. He remembered cozying up on her sofa, staring at the ceiling while she hummed her warmups and applied her makeup. Sometimes she’d work through one of her standards, and Jack would hum or sing along. As he grew up, this progressed to dressing room duets whenever he popped down to the club on rough days. Medda always knew how to cheer him up. 

Knowing that this wasn’t the subterranean club (there were windows!), Jack was hit with the sudden realization that he was getting older. Medda was, too. Eventually, they were going to have to go their separate ways. Jack didn’t want to think about that, so he chose to let the moment sink in.

Without realizing it, he’d started humming an old, familiar tune. He could feel Medda’s smile against his cheek as she pulled him a little closer. “ _I live in a glorious dreamland with you: a kingdom of love set apart,_ ” she crooned along into his ear. This was the first song Medda had sung to Jack when she took him in. It’d held a special place in his heart since—too precious to sing for an audience, but perfect for comfort and that sense of home. 

Jack hummed along through the rest of the song, closing his eyes and pretending he really was ten years old again, plucked off the street by this kind woman. “Thank you, Miss,” he mumbled, leaning into her warmth. “I needed that.”

She patted his back, thankfully ignoring the slight wetness from Jack’s tears on her blouse. Taking his face in her hands, she looked directly into his eyes. “I’ll always be there for you, Jack. Don’t forget that.”

Jack nodded mutely. He feared that, if he opened his mouth, his tears would completely overtake him.

Medda pressed a kiss to each of his cheeks. “I love you. It’s getting late, though, and I still need to spruce up a bit.” She helped lift Jack off the couch, then embraced him again. “Goodnight, son.”

Jack picked up his hat. “Goodnight, Ma.”

She waved as he shut the door behind him. Jack straightened his lapels, made sure his hat was properly placed, and wandered out through the stage door.

Immediately, two arms looped through his own. He paused, taken aback.

Kath and Sarah smiled at Jack from either side of him.

“Hello,” Kath said. “You’ve kept us waiting for a while.”

Jack briefly attempted to extricate himself, but they held on tightly, surprisingly strong.

“We’d just like to talk to you for a little while,” Sarah added innocently.

Jack had a new fear of and respect for Sarah, so he complied. “So, dolls. How’d you like the show?”

“I enjoyed it. That Medda Larkin was the cat’s meow,” Sarah replied. “Kath said she used to perform at your club?”

“I mean,” Jack laughed nervously, “it _is_ called _Miss Medda’s_ for a reason.”

Sarah blushed.

Kath, ever blunt, cut to the point. “You probably want to know why we’re here.”

Jack went wide-eyed. He looked at Kath’s left hand, wrapped around his arm. There was that damn diamond ring, alright. It was almost ostentatious: elaborate but not gaudy.

“You need to talk to my brother, Jack,” Sarah said, point-blank. “This all”—she gestured in the empty air with her free hand—“isn’t quite… what it seems.”

“And,” Kath butted in, “he’s best equipped to explain everything.”

Jack frowned.

“But,” she continued, “I can guarantee that this—” she waggled her hand, highlighting the ring “—isn’t what it looks like.”

Odd. “Um, okay.” Jack wasn’t quite sure what else to say, but he didn’t want there to be any dead air in this conversation. “How’d you all end up with tickets tonight?”

“Oh,” Sarah laughed sunnily. “Kath’s father is a producer.”

Jack recoiled, stunned. Fishing his playbill from his jacket, he opened it to the first page. He skimmed the short list. The only man on it with a last name starting with P was one _Joseph Pulitzer_. “But… there aren’t any Plumbers on this?”

Kath took the playbill from his hand. “Ah, yes.” She let out a light chuckle. “My byline.”

“Your what?” Jack was stunned.

“I’m a reporter, Jack,” she answered. “Being a woman reporter isn’t exactly the most favorably looked upon career. My professional name is Katherine Plumber, but my real name is Katherine Pulitzer.”

Jack reeled, grabbing his playbill back. “Kath Pulitzer. What a name,” he replied, feigning a casual air. Where had he heard the name Pulitzer before? He knew it sounded vaguely familiar.

“Here,” Sarah interjected, “why don’t you come by our place this week? Say, Tuesday? Around noon? We’ll have lunch.”

Jack did not particularly want to see the consequences of turning down Sarah. “Sure.”

“Wonderful,” she said, releasing his arm. “We’ll see you then.”

Kath released his other arm. Jack rubbed at his mildly sore biceps. “Alright, kitten,” she said, taking Sarah’s elbow. “Let’s head home. Goodnight, Jack.”

Jack tipped his hat as he headed north, back to Harlem.

* * *

Jack found that he’d begun spending more time in his dressing room during the day. Sometimes he’d rehearse with Charlie early, grab lunch at a nearby café, and then return to the club with nothing to do besides wait for night to come. He sat at the table, staring at his face in the mirror.

 _Joseph Pulitzer_ . What an uncommon name. Something locked in Jack’s memories prickled. The name sounded big and important. Whatever Kath’s father did, it apparently made him wealthy enough to finance both _The Chocolate Dandies_ and Kath’s extravagant lifestyle. Kath… hold on. Jack dug through the detritus strewn across the table. Finally, he found what he was looking for.

He unfolded the newspaper, previously folded to highlight Kath’s article. Flipping through the pages, he caught the newspaper’s insignia on the second to last one. _THE NEW YORK WORLD_ , it read. _JOSEPH PULITZER……… PRESIDENT_.

There it was. Of course Kath wrote for her father’s paper. And, of course, that had to be why she used a byline. Her father probably didn’t want to deal with accusations of nepotism. He wondered what else she’d written.

Now that he thought about it, Charlie most likely had some sort of subscription. Jack could hear the piano through the door of his dressing room. Opening the door, he strolled casually to the stage, home to the only piano in the club.

There Charlie was, engrossed in the music. Jack felt it filling the air, cutting into his soul. He’d always admired Charlie’s incredible skill, but he rarely got to witness the full extent of it. The melody wrapped around his heart; Jack didn’t want to interrupt him.

Finally, he plunked out the final few notes. Jack applauded gently. Charlie started in his seat, turning to face him.

“That was wonderful,” Jack enthused.

Charlie blushed, scratching the back of his neck. “Thank you.”

Silence hung in the air between them. Jack couldn’t quite figure out how to broach the subject. Luckily, he didn’t have to.

“So,” Charlie began. “What, uh, brings you out here? It’s not that I’m not happy to see you—this is just… not something you normally do.”

“Uh. Mind if I sit?” Jack said, gesturing to the space beside Charlie on the piano bench.

“Sure thing,” he replied, scooting over a bit. Jack slumped down beside him.

“I was wondering—well. Do you happen to have any copies of the _World_ lying around?” Jack figured asking point-blank was his best option.

“Oh!” Charlie grinned. “Yeah. Check the desk in the back—they should be around there somewhere. Why do you ask?”

Jack had to think quickly. “Figured I should catch up on current events, is all. Maybe they’ve repealed Prohibition and I didn’t notice.”

Charlie tried to restrain his mirth. “I think you’d figure that one out pretty quick—your runner’d probably be out of a job.”

Jack rolled his eyes, got up, and gently punched him on the shoulder. “You know what I mean.” Charlie laughed and waved him off.

Jack wandered back to the desk. Yesterday’s paper sat on top, and he flipped through it. Nothing from one _K. Plumber_ appeared in it. He figured it wouldn’t hurt to look through the desk drawers for older copies—papers tended to end up everywhere in it. In the top right drawer, Jack found a few other _World_ copies. He skimmed them, finding the occasional fluff piece on a flower show or musical with Kath’s byline, but nothing of substance. 

At the bottom of the drawer were a few sheets of paper that Jack faintly recognized. Digging them out, he recognized them as the contract Rothstein drafted up. Curious, (it had been several years, after all) Jack read over them. 

Oh, no. Now he knew why the name _Pulitzer_ sounded so familiar. One _József Pulitzer_ was mentioned several times alongside Rothstein and other Jewish mob higher-ups. Could it be that the _World_ ’s Joseph Pulitzer was using an anglicized name?

Jack thought for a minute. He had no idea how Kath and Sarah had met, but he’d seen someone that ostensibly was Sarah at Davey’s previous delivery. If Sarah was involved in organized crime, it could be likely that Kath was too. Especially if her father was this József Pulitzer. Pulitzer’s newspaper money probably also served as a good cover for his mob money. Jack wondered what he’d been involved in first: the paper or the mob?

Of course, this was all hypothetical and depended on Joseph and József Pulitzer being the same man.

No matter what, Kath was certainly an heiress. Why would she bother writing for a newspaper, then? And was she fully financing her and Sarah’s lifestyle, since the Jacobs were lower down the mob food chain? If Jack were that wealthy, he’d want to live alone in a place like that.

Or would he? Perhaps there really was something more between Sarah and Kath, and the engagement ring was simply a cover of some sort. Jack had gotten used to the more laissez-faire attitudes of Harlem, forgetting that not everyone had the same luxuries he did. Luxury! He had to laugh. Very little of his life was what he would call luxurious. 

Jack dug through a few more drawers, searching for more documentation. Some paper clips, several corks, and an old, half-filled flask lay in them amongst several other old newspapers. He sighed, frustrated. What was he going to fill his time with between now and performing? If only there was another way to get more information on this mysterious man.

Another way… that was it! Jack knew exactly what he needed to do.

* * *

Jack lounged in his dressing room, having finished his set for the night. He took a drag on his cigarette and kicked his feet up onto the table. 

Someone knocked gently at the door, tapping out a rhythm that he recognized.

“Come in,” he called.

Specs peered around the door. “They’re here,” he whispered. 

Jack’s plan was working perfectly. “Great. Remember to slide them the note when one of them orders.”

Specs did a mock salute. “You got it, boss.” He shut the door behind him, leaving Jack alone once again.

Jack watched the seconds tick away on Medda’s old clock. He knew he was playing a dangerous game, but by this point he was already in over his head. Besides, he had the upper hand here. Normally he left these things alone. He hoped that the simple surprise of the plan would play to his advantage. 

Jack picked up his unloaded pistol, toying with it for a moment. It wouldn’t hurt to be able to defend himself, so he carefully loaded it, keeping it in reach. Twiddling his thumbs, he hummed quietly to himself as he kept waiting.

The clock insistently chimed eleven.

Jack tensed, grabbing his pistol.

The door swung open. 

Jack didn’t look up. “Howdy, boys,” he said, shining his pistol. “Why don’t you take a seat.”

He heard some shuffling, hoping that his audience obeyed. A tense silence filled the air.

Jack turned around.

“What’s going on, Jackie boy?” Race asked, blasé despite Jack’s gun in his face.

Jack let a lazy grin stretch across his face as he set the gun back on the table. “Is it so wrong for a fella to want to chat with some friends of his every so often? And to take some precautions just in case?”

Spot begrudgingly assented. “You make a point.”

“So,” Jack continued, “how’ve things been? Seems I’m still alive, after all.” He noted a new, faint scar on the side of Spot’s face. Was that from Davey?

“Seems you are,” Race replied evenly. It looked like Spot and Race had decided to be difficult tonight. Or, perhaps, he’d simply managed to start out by pushing the wrong buttons. Bluntness may be his only option.

“You may be wondering why I asked you to meet me here,” Jack said. 

Spot and Race nodded, mute.

“Since you were so kind as to…” Jack paused. He wasn’t quite sure how to phrase this without implying that he had indeed seen them in the alley the previous week. “…Tip me off about some potential trouble—”

“Spit it out,” Spot interrupted.

“Okay, okay. Was wondering if you knew a cat by the name of Pulitzer?”

Race blanched slightly. Jack caught Spot elbowing him subtly. “That’s quite a name, pal,” Spot said. “Interesting one to be familiar with.”

Something was up. Spot and Race had to know that Jack was catching on. 

“Interesting, indeed,” Race parroted.

Then again, how willing were Spot and Race to blow his brains out before revealing any of this information? Maybe this plan wasn’t as well thought out as Jack thought. He did have one ace up his sleeve, though.

“I know he’s with Rothstein. He’s on my papers,” Jack tried.

Race breathed a very visible sigh of relief.

“I’m just curious about some of his ties, is all.”

Race tensed again. Spot leaned over to whisper something in his ear, gently rubbing at his knee. 

“What do you want to know?” Spot asked gruffly. Jack internally cheered for this small victory. He must’ve known that he was cornered.

“He doesn’t happen to have any… relatives with similar names, does he?” Jack sincerely hoped they’d get what he was hinting at.

Race laughed, defusing the tension. “Y’know most people like us weren’t born here, right? Changing our names is necessary in certain circles.”

Interesting. Perhaps that was how Spot, a clearly Italian man, had ended up with an Irish surname.

“Makes enough sense, I suppose.” Jack thought for a minute. “Just curious—what kinda language does a name like”—he wasn’t quite sure how to pronounce it—“József come from?”

Spot grimaced. “You don’t get out much, do you?”

Jack was confused. “What do you mean?”

“Think I have any more of an idea than you do?” Spot shot back. “We keep to ourselves so we don’t kill each other.”

“But,” Race chimed in, “if I had to guess, it’s something European. Probably immigrated here and realized that a name like that isn’t exactly good for business.”

“Understandable.” Jack took a moment to process. “Have you met him?”

Race cackled loudly. “You kidding? We couldn’t even look at a guy like that. They’d shoot us on sight.”

“Jackie, you gotta understand something,” Spot added. “Men like Pulitzer are untouchables in our world. If you see them, you know you aren’t leaving alive.”

“Okay, okay, I get it,” Jack said. A thought occurred to him. “Wait a minute. If you all don’t cross each other’s tracks… how does something like”—he gestured at Spot and Race—“what you have work?” 

Race started. “What we have?”

“Oh, palooka,” Spot chided gently. “This”—he gestured between himself and Race—“barely exists outside your place.” He turned to face Race. “I wish it didn’t have to be that way, but for now we pass as two twentysomething bachelors that happen to share an apartment.”

Jack felt like he was intruding on something extremely intimate. “I’m, uh, I’m real sorry about that.”

Race gently slapped Spot on the knee, returning their collective focus to Jack. “Thanks, amico,” Spot answered.

Race looped his arm in Spot’s. “Now, Jackie boy, we hate to leave you all alone, but we have some personal business to attend to.” They got up off the couch, bidding Jack a final farewell, and almost too casually wandered out the door. Jack had to close it behind them.

So these two Pulitzers really were one and the same, if Spot and Race were to be trusted. That made Kath even more of a dangerous figure than she had already seemed to Jack. Newspaper _and_ mob heiress Kath, who had been simply an intimidating journalist just a month ago. Newspaper heiress, mob heiress, and reporter Kath, who happened to be engaged to one David Jacobs, if Jack was reading the signs right. Wait.

If József Pulitzer was such an “untouchable,” how the _hell_ had Sarah and Davey, two very low-ranking mobsters, managed to fraternize with Kath? And how was Jack not dead for knowing her?

**Notes for the Chapter:**

> thank you all so so much for reading and keeping up with this!!  
> some historical notes:  
> jack and medda's song is To the End of the World With You by Henry Burr. you can listen to it [here](https://youtu.be/FLRQ86X2Uaw)!  
> technically at this point the new york world wasn't called that - it was an evening paper, called the Evening World. however, i wanted to keep a tiny tie to the actual canon of newsies so i didn't change it lmao  
> józsef pulitzer is joseph pulitzer's name in hungarian, aka his non-anglicized name!  
> also!! did a little more research on the harlem renaissance, which would be just beginning at this point. harlem was much more welcoming to lgbt+ people than most other places in NY, even having prominent performers that were wlw or gnc!! (look up gladys bentley for one of my favorite examples of this!)  
> hope you all enjoyed!! please leave a comment with any thoughts/concerns/etc you have!!  
> and don't forget! i'm @landlessbud on tumblr - please RB [this post](https://landlessbud.tumblr.com/post/621857494037299200/the-substitute-iim-david-he-mumbled-eyes-on) if you're enjoying this fic!


	7. Chapter 7

**Summary for the Chapter:**

> Jack pays a long-overdue visit.

Kath and Sarah’s apartment building loomed before Jack. He couldn’t figure out quite why it was so intimidating until he remembered that this was the first time he’d been there during the daytime. 

Jack checked his pocket watch. One fifty-eight. Close enough. He worked up the nerve to approach the front door, jabbing quickly at the buzzer.

The door clicked open, and he went inside. He took the stairs slowly, anxiety building. Why would Kath and Sarah want to meet with him in broad daylight? Now that he thought about it, were they planning to kill him, it’d be easier for them to dispose of his body here than in Harlem. Few people knew that he ever left Harlem, and fewer knew where Kath and Sarah’s apartment was. Was Jack walking to his death?

Then again, Kath and Sarah had generally been kind to him. They’d never shown any intent of killing him—Sarah hadn’t even when she didn’t know he was watching her. Jack thought back to that night. Why had Spot and Race even been in that alley in the first place?

Before he knew it, Jack was once again at the door to apartment 5B.

If he was going to his death, might as well get it over with quickly. He knocked gently at the door three times— _ tap-tap-tap _ .

“Welcome back, Jack!” Sarah exclaimed, opening the door. “Come on in.” She led him through the gorgeous parlor to a set of curtains he hadn’t noticed before. Pulling them aside, she revealed a pair of French doors, which opened into a smaller dining room.

Gilded plates sat atop a white-clothed table surrounded by ornately carved wooden chairs. A silver covered dish—something Jack had only seen the occasional photograph of—sat in the center of the table. Kath slunk in through another door that probably went to the kitchen and took a seat in the chair to Jack’s left. Sarah took the seat opposite her, leaving Jack the spot facing directly away from the glass doors. He did not like the look of this, but he took his seat, trying not to gawk at the red velvet-textured wallpaper and crystal glasses. 

Sarah poured a clear liquid into her glass from a silver pitcher, then passed it to Jack, who eyed it suspiciously. “What’s that look?” she asked him, laughing a little. “I’m not one for day drinking. It’s just water, don’t worry.”

Jack knew any hesitation could give him away. He needed to stop second-guessing everything. Laughing with her, he poured himself a glass of water. “You can never be too sure.” He hoped his joking tone would avert any of Sarah and Kath’s suspicions.

Sarah smiled at him fondly. Jack passed the pitcher to Kath, who silently poured herself a glass and set the pitcher down next to the empty fourth seat. 

“I hope you’re not a vegetarian,” she said, lifting the cloche to reveal three small roast fowl.

Spying Jack’s quizzical look, Sarah clarified. “They’re ducklings. Our favorite, so we figured you’d like them. The sauce is simply the clam’s garter.”

Sure enough, they were drizzled with an orange sauce that smelled divine. And were those cranberries, too?

While Jack salivated, Kath served everyone their own duckling. Once she’d finished, she set the cloche back on the dish. “Dig in.”

Jack happily obliged, picking up his fork and knife. The meat melted on his tongue. He was in heaven. Sarah and Kath giggled, probably because of Jack’s blissed-out expression. So maybe he didn’t go out to fancy places much, and maybe he just couldn’t process how incredible the meal in front of him was.

He looked up from his plate, mouth full. “It’s real good.”

Kath snorted, and Sarah almost fell over laughing. Jack blushed, then continued shoveling food into his mouth. He’d already lost most of his dignity anyway.

With a final  _ clink _ of silverware on china, they all managed to clear their plates. Sarah lifted the cloche, stacked the plates on the tray underneath, replaced it, and took the whole thing out through the kitchen door. She soon returned, probably having set it on a counter somewhere without washing it. Jack wondered if they had people to do their dishes for them.

They sat in a companionable silence for a few minutes. Jack figured it was probably time to take his leave. “It’s been lovely, dolls,” he said, scooting his chair back. “Thanks for having me.”

The French door behind Jack opened with a slight  _ snick _ .

“Not so fast,” threatened Davey from behind him as Sarah and Kath aimed matching pistols at Jack.

Jack raised his hands in surrender. Davey sauntered around the table to lean on the empty chair opposite Jack. “You can put your hands down. Relax. You’ll be here for a while,” he continued.

Jack lowered them, scooting back towards the table. “Do, uh. Do you have to keep pointing those at me?” He swallowed nervously, nodding towards Sarah and Kath’s guns.

“Yes,” Kath replied, infinitely more menacing than she had been just moments ago. “You have to swear on your life that you won’t breathe a word of what we’re about to tell you.”

Sarah’s piercing stare bored holes into Jack’s soul. He looked into Davey’s eyes—they were impassive. Why did he have to choose this man to fall in love with?

Jack hadn’t put two and two together until that moment. Davey had always had an undeniable draw, but Jack figured it was his nervous, naive nature that drew him in. Now he knew better. He’d seen Davey in that alley, probably trying to protect Jack’s life the only way he knew how. Maybe Jack didn’t need a knight in shining armor, but a mobster with an uncanny skill with guns seemed rather ideal.

“So?” Sarah’s sudden shift in tone frightened Jack. He’d never heard her be anything but cheerful and bubbly, though he had seen her that one night in the alley…

“I—I swear.” Jack’s life was already on the line with the speakeasy, so what was one more secret?

Sarah and Kath tucked their guns away, and Davey slumped into the fourth chair.

“What shall we start with, David?” Kath asked, turning to Davey. Jack eyed her left hand. The ring was still there. Did he dare interrupt?

Davey rubbed at his eyes with the heels of his palms, then blindly waved at Kath. “I dunno. You choose.”

Jack chose this moment to pipe up. “Um. So. What’s going on with Kath’s ring?”

“Thank you for your input, Jack.” Davey yawned and stretched a little.

“Late night?” Sarah teased.

Davey rolled his eyes. “Don’t remind me,” he groaned.

“So? My ring?” Kath reminded him.

“Yeah, yeah, I’m getting to that. Jackie, first thing you gotta understand is that a hell of a lot of what you know about me isn’t true.” Davey showed none of what Jack had thought to be his trademark anxiety. What was going on?

“Uh. Alright.” Jack did catch the pet name, though, so he figured Davey at least didn’t hate him. Now that he thought about it, he’d probably be dead by now if Davey hated him.

“To answer the question you haven’t asked, yes, that  _ is _ an engagement ring.”

Scratch that. Jack wanted to throttle Davey, then Kath. Then probably Sarah for allowing this to happen.

“Relax, Jack,” Kath interrupted. “He isn’t done.”

“Kath and I don’t want to be engaged.”

Was it too dramatic of Jack to gasp? Perhaps. Did he gasp anyway? Perhaps.

“There’s been… an expectation of us for a long time. For us to eventually settle down together, get married, the whole shebang. We’d been trying to hold off the engagement for as long as possible, but certain circumstances made that… impossible.”

“Kath’s father has never been particularly pleased about our living situation,” Sarah interjected. “He was getting a little too suspicious of our involvement, so Davey had to step in.”

Jack needed a moment to process. “Wait, wait. Okay. Kath’s father, who happens to be  _ Joseph fucking Pulitzer _ ? The newspaper guy? Who’s also on my moonshine papers?”

“I  _ told _ you he’d figure that one out,” Kath grumbled to Sarah. “You can’t keep spilling the beans like that, kitten.”

“But it’s  _ Jack _ ,” Sarah pleaded, doe-eyed. “He doesn’t have anybody to tell, anyhow.”

“I’m right here,” Jack said, moderately insulted.

Davey cleared his throat. “Shall I continue?”

Sarah and Kath mumbled their assent. Jack had never seen Kath look cowed before.

“So. I stepped in and proposed to Kath. You have to understand, Jack—there’s nothing romantic between us. Never has been. I don’t exactly swing that way, and Kath… well. Kath’s always been goofy for Sarah.”

If Kath had “always” had eyes for Sarah, that’d have to mean they’d known each other for a long time. Yes, the puzzle of Davey Jacobs was slowly coming together, but Jack found there were more pieces missing than he thought. 

Wait. Davey didn’t “swing that way”? A glimmer of hope returned to Jack’s heart. Hopefully Davey was insinuating what Jack thought he was insinuating.

Jack opted to pose the first question that came to his mind. “Wait. So. How long have you all… known each other?”

Sarah laughed. “You’re quite slow on the uptake, aren’t you?”

Jack furrowed his brow.

“We were practically raised together. I don’t know a time when I didn’t know these two,” Kath said.

If they’d known each other for their entire lives and Kath’s father was some kind of “untouchable”… had the Jacobs always been punching above their weight? Or was there a bigger secret behind this?

Spotting Jack’s confusion, Davey jumped in. “Before I tell you this, I want to apologize. I hated to keep this from you, but it’s life or death for me and my family when even one more person knows.” He took a deep breath. “I’m not new to the mob, Jack. I was raised in it. So was Sarah. Our dad is Rothstein’s… secret agent, if you will. His anonymity is what makes him so powerful. Nobody outside Rothstein’s inner circle knows who he is. But… he’s getting on in years, and…”

Jack could not believe his ears. First, that Davey had been a mob man this whole time. He wondered what it must be like to have your life planned out for you by the moment you were born. And that Mayer, that kind, soft-spoken man, was actually the most dangerous person he’d ever met. Had he been on Rothstein’s hit list for years? And why had Davey taken over Mayer’s runs?

“So… you replaced him as my runner?” Jack voiced his final concern. “Why?”

Davey pinched the bridge of his nose. “You know the mob places a huge emphasis on hereditary roles, right?” He looked up, directly into Jack’s eyes. “I’m his replacement.”

Jack was stunned. “You?”

Several pieces of Davey’s puzzle fell into place. Spot and Race’s reaction to his appearance, the moment in the subway, the confrontation in the alley… Davey’s evasiveness started making more sense. But why did he hang around Jack so much even when it wasn’t necessary, like at Medda’s opening night? Further, why had Mayer had to watch over Jack’s club in particular for so long?

Davey looked at Jack with sad eyes. “You have to understand. I haven’t had much of a choice in any of this.” He laughed humorlessly. “But a job’s a job, y’know?”

“I… suppose.” Jack had no idea how to respond beyond that. The more he thought about it, the more he realized that he and Davey were in similar boats. Jack hadn’t ever considered taking a job outside the speakeasy, but he did need some sort of income to survive. There was still the question of Sarah, though—what was she doing in the mob? “Speaking of, um, jobs,” Jack continued, “Sarah, pardon me for being so blunt, but what… do you do?”

“Sarah… for lack of a better term, is Rothstein’s back-up plan,” Davey replied. “It was pretty convenient for him that our dad just happened to father twins. In fact, he figured that Sarah would be even deadlier than I was, since she’s a girl.”

Jack winced a little.

Sarah rolled her eyes. “Don’t worry, Jack. You’d be dead already if we wanted to kill you.”

Somehow, that wasn’t particularly comforting.

If Sarah and Davey were Rothstein’s most dangerous young agents, what the hell were they doing running Jack’s deliveries? Bootlegging didn’t seem to be the riskiest mob activity to partake in. There were people whose entire job descriptions were  _ murder _ , after all.

“Great. Uh, thanks for that, I guess. Also. No offense, but why were you, of all people, running my moonshine?”

Davey closed his eyes and took a deep breath. “You’re our biggest liability. Our biggest fucking liability.”

Jack didn’t understand.

“Remember those negotiations you had with Rothstein? Yeah. You didn’t know it, but the price you paid for that much freedom was our  _ constant surveillance _ . Getting that much booze up to fucking Harlem at that time of night without being caught ain’t easy, pal. And once they got word of it, the Italians and Irish put guys on your case, too. If we go down,  _ everyone’s _ going down. You get me? Rothstein’s the linchpin in the system. If you made one wrong move, you’d ruin this entire fucking city, and everyone’d be out for your blood.”

Jack’s blood went cold. That must’ve been why Spot and Race hung around so much. Could he trust them, then? Or was their “friendship” purely of a protective nature? Granted, Race seemed to be too bad of an actor for their entire relationship to be based on lies.

Davey seemed to realize he’d been a bit harsh on Jack. “I’m not trying to scare you. I’m just trying to show you my understanding of the situation. I know it’s not easy. There’s a lot on my shoulders, too—but being aware of the extent of a situation tends to comfort me, if that makes sense.”

Jack nodded, too overwhelmed to form words.

Kath reached over and squeezed Jack’s shoulder reassuringly. “We care about you, Jack. That’s why we’re here.”

“But,” Sarah interjected, giving Kath a pointed look, “we should probably take our leave.”

She and Kath got up and slipped through the French doors, closing the curtains behind them. Jack and Davey were left completely alone.

“Hey,” Davey said gently.

Jack looked up. Davey’s arm stretched out on the table, palm up. An offering. Jack took his hand.

“Why… how did I believe so many lies?” Jack asked, looking back down at the table. Vulnerability was not his favorite activity.

Davey rubbed the back of Jack’s hand with his thumb. “You’re not the only performer here, you know. And,” he laughed, “I really did get lost that first night.”

Jack allowed a small smile. “Nothing else?” he teased, hinting at a confidence he didn’t have.

Davey blushed. Jack had never seen him truly flustered like this before. “Maybe there was this real looker of a fella there, and maybe I’d started to carry a torch for him,” he admitted. 

Davey had been interested in him from the beginning? Wait. He’d been interested in  _ Davey _ from the beginning. It’d taken him a while to realize that. Jack thought moments like these only happened in romance novels or cheesy musicals, not real life.

“Could I ask you something?” Jack figured now was as good a time as any to bare his soul.

“Anything,” Davey murmured.

Jack looked up, catching Davey’s eyes. “Can I kiss you?”

Davey’s eyes went wide, and for a moment Jack feared he’d misinterpreted the situation. Then he nodded, slowly at first but quickly gaining enthusiasm.

Jack got out of his chair, never once releasing Davey’s hand.

Once Jack had rounded the table, Davey pulled him onto his lap by their connected hands. Davey’s face was so very, very close.

“Is this okay?” Davey breathed into the small yet too-far distance between them.

Jack decided to take the initiative for once and closed the gap between them. He poured all of the tension and confusion and frustration of the past month and a half into the kiss, thankful that Davey was fervently kissing back. His heart soared, and he felt lighter than he had in a long time. Davey tasted of cigarette smoke; Jack couldn’t get enough.

They broke for air. Davey tenderly rested his forehead on Jack’s. “You mean more to me than you know,” he whispered.

Jack’s heart fluttered. A hot tear rolled down his cheek as he allowed the weight of the past hour to sink in. Davey took Jack’s face in his hands, wiping away the tear. “I won’t let anything happen to you, okay?”

Jack nodded, trying to hold back any more tears.

“HEY!” Sarah yelled from the parlor, ruining the moment. “YOU LOVEBIRDS DONE IN THERE?”

Jack looked into Davey’s eyes. “I SUPPOSE,” he called back. “C’mon,” he murmured, pulling Davey up with him. “We’ll have plenty of time for this later.”

Davey wiggled his eyebrows suggestively, making Jack laugh. They opened the doors into the parlor, only to be greeted by Sarah and Kath lounging, almost pretzeled together, on one of the velvet sofas.

“It’s about time,” Kath said, gleefully noting Jack and Davey’s intertwined hands. “Come over here,” she beckoned, gesturing at the sofa across from her and Sarah’s.

They obliged, and Jack threw his legs over Davey’s lap. “This okay?” he asked. Davey quietly consented, looking down at Jack fondly. Jack had never felt safer than he did in this moment.

“So, boys.” Sarah grinned. “Got any plans for this evening?”

“Oh, I don’t know,” Davey replied, squeezing Jack’s knee gently. “I was thinking of heading uptown to see this guy perform—I hear he’s the oyster’s earring. Name rhymes with Smack Jelly?”

**Notes for the Chapter:**

> HOOOO BOY. thank y'all so much for reading this!!!! the secrets have Finally come to light!  
> there's really no historical evidence for this chapter, but the wallpaper in the dining room is based off of the wallpaper in the morgan library in NYC bc i think it's really pretty.  
> roast duckling was apparently a thing people ate in the 1920s according to a very brief google search of mine.  
> and yes, oyster's earring and clam's garter are real phrases according to one of my five tabs of slang references.  
> you may also have noticed that i do, in fact, know how long this fic will be - look forward to one more chapter in the near future.  
> hope you all enjoyed!! please please please leave a comment with anything - your thoughts, concerns, etc!  
> thank you all again! i'm @landlessbud on tumblr - please rb [this post](https://landlessbud.tumblr.com/post/621857494037299200/the-substitute-iim-david-he-mumbled-eyes-on) if you're enjoying this fic!


	8. Chapter 8

**Summary for the Chapter:**

> Jack learns that every rainy day eventually pays off.

That night, Jack painted his signature Customer Service Grin across his face, waving at the cheering crowd. Charlie plunked away at the piano as Jack introduced himself and his performance. He looked over the audience, trying to spy familiar faces. Before he caught anyone, he heard his cue.

“ _ You’re the cream in my coffee… _ ” Jack wasn’t above reusing songs in his set. The audience wasn’t the same every night, anyway. He kept searching, trying to find who he was looking for. “ _ You’re the sail in my loveboat… _ ”

Finally, he found Davey, once again in the front row. Jack gave him a wink, spotting Sarah and Kath on either side of him. He hoped he wouldn’t be too distracted knowing Davey was watching him the whole evening. Though, if this afternoon were to be taken into account, that may be too high a bar for him to reach.

Jack breezed through the next few songs, perhaps looking at Davey a little too often. Now, he figured, was a good time to work the crowd.

“How’re you all doing tonight?” he crowed to the club. Some laughs, cheers, and wolf whistles came back at him. “Fantastic,” he continued, stretching out the vowels. “I thought I’d give you a little treat tonight—how about a new song, since you were so kind as to come out on a Tuesday?”

The audience whooped and hollered back at him.

“Alright, okay. I can work with that.” Jack laughed genuinely. He’d been practicing this song for a few days now—Buttons had caught a performance of it at another club and insisted it would sound beautiful in his voice. She had to have known it was written for a female performer, but Jack couldn’t be bothered to change the pronouns. He figured his audience wouldn’t care too much anyway. 

He nodded to Charlie, who began the vamp as Jack shook out his limbs and stepped back up to the mic. “ _ Who’s there? Who’s there? Stop bangin’ on my door! _ ”

The speakeasy filled with uproarious laughter. Jack didn’t often perform particularly character-y songs, so placing one smack in the middle of his set was a nice change of pace. Plus, it let him try out his acting chops—maybe one day he’d see a big Broadway stage like Medda.

Jack made sure to catch Davey’s eye. “ _ It might be quite alright tomorrow night, but my baby’s here tonight—he’s busy and you can’t come in! _ ” He winked, and the crowd went wild. It was looking like he’d have to keep this one as part of his set, then. He risked one more glance to the front row.

Davey was clearly biting back a grin, cheeks a little red—was that a blush or the booze? Jack let the high of having affected his—lover? boyfriend? they hadn’t discussed what exactly was happening between them—carry him through the rest of his set.

“Now, folks, the show isn’t over yet.” Jack had rushed home from the Lower East Side with his head in the clouds, still overwhelmed with emotion. He’d finally worked up the courage to ask Charlie and the band to learn another new song. “I’ve got a special surprise for you—it’s an old favorite of mine. Miss Medda’s, too. Here, uh. Well. Here goes. It’s been a wonderful night!”

Jack turned to the band. How the  _ hell _ had Albert managed to scrounge up a violin in the past four hours? Had he been holding out on Jack the entire time? The number of instruments that man could play was absurd.

Jack settled into the waltzy vamp, immersing himself in the music. He pretended his only audience member was Miss Medda and began.

“ _ A wonderful power has entered my life—it came when your eyes reached my heart. I live in a glorious dreamland with you: a kingdom of love set apart. _ ”

He sank into the music, becoming one with it. Jack closed his eyes as the song continued so he wouldn’t accidentally burst into tears before it ended.

“ _ My heart will bid me go, dear, to the end of the world with you, _ ” he finished, finally opening his eyes. “Thank you all!” he called out, bowing. “Have a good night! Don’t get me in any trouble out there,” Jack cautioned, making his way offstage. 

He let the roar of the crowd carry him to his dressing room, where he immediately pulled off his tie and unbuttoned the first couple of buttons on his shirt. Sinking back into the chair he’d gotten to match Medda’s old sofa, Jack let the stress and tension from performing melt away. He didn’t owe anyone anything now, least of all the patrons at  _ Miss Medda’s _ . Losing himself in thought, he wondered how Medda would’ve reacted to his performance. Was it a bad idea to share their song with a big audience like that? If it had been, Jack placated himself with the fact that it was too late now to do anything about that.

What a day he’d had. The weight of everything he’d learned about Davey (and Kath and Sarah by extension) had sat, heavy, on his shoulders since he left Kath and Sarah’s apartment. Davey,  _ his _ Davey, held so much power in his hands that it stunned Jack. And the knowledge that if Jack ever made one wrong move, he’d be dead… Well. He’d already known that. He just didn’t realize how  _ many _ people would want him dead should that happen.

A gentle knock at the door shook him out of his imminent downward spiral.

Jack tensed, reaching for his gun. “Hello?”

“Coffee?” a voice called, muffled by the door. “It’s cream.”

Jack relaxed, laughing. “Come on in.”

The door opened, revealing none other than one Davey Jacobs. He closed the door behind him as Jack realized that he’d never been in his dressing room before. “Here. Uh. Sit.” Jack got up from his chair, took Davey by the hand, and pulled him down onto the larger sofa with him. Davey honest-to-god giggled, and Jack took the opportunity to throw his feet up onto his lap. 

Davey tapped Jack on the nose. “You, sir, were simply the tiger’s spots up on that stage tonight.” Jack jokingly swatted at Davey’s hands, blushing. “I’m not kidding, baby.” Davey caught one of Jack’s hands and kissed his knuckles gently.

Jack wouldn’t admit it, but he melted. He did, however, remember that there were some questions still left unanswered. “So… what are we?”

Davey paused. “What do you want us to be?”

Jack couldn’t quite figure out how to word the way that Davey’s essence had crept unassumingly into his dreams, then his waking hours, then his entire being and filled a hole he didn’t know existed in his heart that left him aching for more. Instead, he figured concision was his friend. “I want to be yours.”

Jack wished there was some way to forever capture Davey’s sharp intake of breath at that. “Then I am yours,” he whispered back, awestruck.

Jack tugged on Davey’s hands, pulling him down on top of him. “Is this okay?” he breathed, eyeing Davey’s lips.

Davey closed the gap between them in place of an answer. Jack sighed into the kiss, letting Davey’s weight pin him to the sofa. Here, in Davey’s arms, he was secure. He didn’t have to fear for his safety, and he knew Davey would be gentle with him. Davey, Davey, Davey. Davey consumed his senses. Jack couldn’t remember a time when he’d allowed himself to just relax and actually enjoy a blissful moment like this one.

They broke for air. Davey hummed, eyes intent on Jack. “You’re beautiful, you know that?” he murmured. 

Jack blushed and turned away slightly.

Davey, apparently, took this as an opportunity, beginning to kiss down Jack’s exposed neck. He threw his head back in ecstasy, eyes closed. Jack could feel Davey grinning against his collarbone as he discovered how far unbuttoned Jack’s shirt already was.

The door to Jack’s dressing room clicked open, and Davey turned on a dime, still entangled with Jack but now pointing a gun directly at the crack in the door.

“Sorry!” a muffled voice exclaimed. The door shut with a slam. 

Davey tucked the gun back in his waistband and heaved himself up, pulling Jack upright with him.

“Rain check?” Jack asked with a sarcastic yet sad smile. He began to button his shirt and smoothed his hair a bit.

“Of course,” Davey replied, pecking him tenderly on the cheek. Jack watched him attempt to unmuss his tousled hair and straightened Davey’s bowtie, which had been knocked askew as they cavorted.

Jack took a look at himself and Davey in the mirror. Good enough. They didn’t have the time to get any more put together, so Jack hoped their still somewhat disheveled state would go unnoticed.

Jack stood up and brushed himself off. “Ready?” he whispered, turning back to Davey.

“As I’ll ever be, I suppose.”

Jack cautiously approached the door, listening for whoever was on the other side of it. Behind him, he could hear Davey toying with something mechanical—almost certainly his pistol. He put his ear to the door. Nothing came through.

“Hello?” he said, still listening carefully.

“You decent in there?” Race answered.

Jack peeked around the edge of the door, opening it a crack. Race and Spot stood in the hallway, hats low on their foreheads. Jack double-checked the hallway, ensuring they were alone, gave Davey a silent thumbs up behind his back, and opened the door. “Come on in.”

Davey, at this point, had settled back onto the sofa, leaving the matching armchair and Jack’s director’s chair at his makeup table open.

Race bumbled over to the armchair, and Spot opted to sit in his lap. Jack shut the door, returning to his spot beside Davey but maintaining a respectable distance from him.

“What, uh, brings you here?” Jack asked, attempting a blasé demeanor.

“You’re not dead,” Spot shot back, point-blank.

“Clearly not.”

“Why’s your runner here?” Race interjected. There was something hesitant in his voice that Jack couldn’t quite place.

Davey fixed a stony glare on him. “Why are you here?”

Jack was too tired to deal with the building tension. “Leave the Mouth alone, boys. What brings you here?”

“Something wrong with congratulating a pal on a good performance?” Spot retorted.

Alright, so things would be tense no matter what.

Jack turned to Davey. “Go tell Sarah and Kath to stay after we close. Things should be fine by the time you come back,” he whispered.

Davey nodded, getting up. The door clicked shut behind him.

“What’s going on, boys?” Jack hoped his no-nonsense tone would keep them from spouting lies.

“You—we thought you were in  _ danger _ because your fucking runner was hanging around so much!” Race spluttered.

“What can I say?” Jack replied, attempting to imitate Davey’s cool demeanor. “We’re all Ethels here, aren’t we?” He pulled out his pack of cigarettes and lit one, taking a drag.

Jack wished he had a color camera to capture how red Spot and Race’s faces were.

Spot regained his composure more quickly than Race. “And what about it?”

Jack noted the way Spot subtly took Race’s rapidly tapping hand, soothing him. Being forward wasn’t going to get him anywhere. He took another drag off his cigarette. “Want one?” Jack offered the box to Spot and Race.

“Thanks.” Race reached over Spot to take one, pulling out his own lighter and igniting it. Jack watched the tension melt away from his shoulders.

The grandfather clock chimed. Twelve thirty. Race started, choking on his cigarette. Spot patted his back gently as he coughed. Jack heard the door click open and silently prayed that it was Davey.

Spot and Race froze. The door creaked open and shut, and a gentle weight settled beside Jack on the sofa. 

“Hello, boys,” said Kath. She smiled, something dangerous glittering in her eye.

Race hastily stubbed out his cigarette. “We were just leaving.” 

Spot hopped up, pulling Race with him. “Nice seeing you.” They scrambled out the door, slamming it behind them.

Kath laughed, wrapping an arm around Jack. “How’re you doing?”

He took a moment to think. “Better. But still exhausted. Haven’t really gotten a moment to myself all day.”

“Ah.” Kath moved to leave.

“Wait!” Jack cried. “Before you go—remember to stay ‘til after we close. Let Mush and Specs know I gave you the okay.”

Kath nodded with a tender smile. “See you soon, Jack.”

The door clicked shut behind her, leaving Jack finally, blissfully alone. 

He let himself zone out, humming the occasional standard.

Finally, the clock chimed one. Jack buttoned his shirt back up to show a more appropriate amount of skin and left his bowtie on the table. He’d learned to leave a good majority of the clothes he wore onstage in his dressing room. That’s what it was for, after all. 

Wearily, he opened the door and wandered down the hidden hallway to the main club. Smalls spotted Jack first, toasting to him from the bar. “Here he is!”

Jack allowed a tiny, tired smile. “Hey, folks.”

The small assembled crowd cheered. Sarah waved him over to the conspicuously empty seat beside Davey and practically shoved him in it.

“You doing okay?” Davey asked quietly.

Jack gave him a slight nod, then leaned his head on Davey’s shoulder. “Professor!” he called jokingly.

Mush sidled over. “You rang?”

“Get me two shots of the strongest hooch you got.” Jack caught Davey eyeing him worriedly. “Don’t worry. It’s still pretty watered down.”

Sarah threw back her head in laughter. Noticing the sudden silence in the speakeasy, she sighed. “What? That  _ was _ pretty funny.”

Kath kissed her lovingly on the cheek, and everyone resumed their conversations.

Mush slid Jack a mug. “Should be about two shots in there. We’re a bit low on mugs at the moment—you’ve attracted quite the following.”

Jack blushed but gratefully took the drink, tossing it back in two swigs.

“So, Jack.”

He turned to Sarah. “Hm?”

“I have a proposition for you.”

Jack’s exhausted brain did not have the level of function necessary to process this statement. “A what now?”

“ _ Phrasing _ , Sarah,” Davey warned.

Sarah giggled. She’d probably had more to drink than Jack at this point. “Come back to our party this weekend. We’ve missed you, and we know you can get a night off.”

Jack mulled over the idea. “The only night I took off was for Medda’s opening night, and Saturdays are pretty big here…”

“Go, you boob,” Buttons interrupted. “We can hold down the fort here for you. You deserve a day off.”

Jack was still hesitant. “I don’t know…”

“C’mon, baby. You’ve earned it,” Davey purred into Jack’s ear.

Jack put his hands up. “Fine, fine. I give up. I’ll go.”

Kath gently slapped him on the shoulder, and a couple others clapped.

“That’s a first,” Specs exclaimed. “Never seen Jack Kelly give in to reason before!”

Jack laughed. “Sure, sure. Now get me another drink!”

* * *

“ _ I can see it’s up to me to give you some advice, _ ” Jack began.

Sarah chimed in. “ _ Yes, I fear when winter’s here, you’ll offer me some ice. _ ”

Jack didn’t know how he’d forgotten the rush of singing in Kath and Sarah’s parlor. Here, he could metaphorically let his hair down and not worry about how his song choices would affect the profits of the club. And, though the room tended to be filled with a haze of cigarette smoke, he could actually see his audience and all of his surroundings.

Plus, no offense to Charlie, this piano had a much fuller sound. Jack relished Sarah’s musical skill and loved how easy it was to riff off of her performance.

Jack was taking a water break when a sudden realization hit him like a brick wall. This place was now another home to him.

Or was it the people?

Kath and Sarah had so kindly opened up their home to him and given him so much more artistic freedom than he’d ever had before.

And Davey… 

Davey was his anchor. Jack didn’t know how else to phrase that. Davey was a happy weight on his heart, tethering him to reality and the explosion of feelings that existed within it. Jack never felt safer than when he was with Davey. He admired Davey’s outward ferocity and inward genuine, personal tenderness. For the first time since Miss Medda left the club, Jack knew he had someone who would always listen and always understand. Davey’s mob role contributed to what Jack loved most about him: that intense privacy he cultivated that magnified every feeling Jack had for him.

At Sarah’s request, Jack had brought back her favorite part of his set from Tuesday. “ _ I’m busy and you can’t come in! _ ” he warbled to the small crowd’s amusement. Davey, again, turned beet red, only managing to hide part of his face by burying it in Kath’s neck. Jack grinned as he finished out the song, and he could hear Sarah cackling with glee at the piano.

Of course she’d asked him to sing that again to embarrass her brother.

A few songs later, their audience was thinning out. Jack felt dead on his feet. “One more?” he mouthed to Sarah. She nodded and gave him a thumbs up, beginning a gentle ballad. Jack let the melody sink into his bones and relaxed minutely. This was another song he’d first learned from Medda, and, upon his discovery that Sarah also knew it, he insisted upon a slight modification of the song to become a duet. Sarah’s songbird tone fit perfectly for the harmonies and flourishes they’d added.

“ _ It had to be you, wonderful you. It had to be you! _ ” he sang, closing out the song. 

Sarah scatted along, joining with him for their final harmony: “ _ Just you. _ ”

People began to wander out of the apartment as Jack and Sarah thanked them for listening. Soon, only Kath and Davey, still somewhat entangled on their sofa, remained.

“So,” Davey said, eyeing Jack. “How about that rain check?”

**Notes for the Chapter:**

> it's 1:15 am but i wanted to be DONE so here it is! the final chapter of the substitute!  
> some historical notes:  
> here's a [link](https://www.youtube.com/watch?v=IqaNW6TwT0U) to You're the Cream in My Coffee, which i realized i never gave y'all.  
> the next song Jack sings is I'm Busy and You Can't Come In by Alura Mack. you can listen to it [here](https://www.youtube.com/watch?v=GcqeNvIl-7s).  
> jack, again, closes out with To The End of the World With You (link's in chapter 6!).  
> Ethel is 20s slang for an effeminate man, by the way  
> Jack and Sarah sing You'll Never Get to Heaven by Aileen Stanley and Billy Murray (listen to it [here](https://open.spotify.com/track/1kAzBdxal9dQ2JvmULtiEt?si=gEui-RIuSzulnoVZq8s5eA)) and Aileen Stanley and Billy Murray's version of It Had to Be You (listen to it [here](https://open.spotify.com/track/0K1TGYwO92Nc6mdBjAktnn?si=i7c-Dn50ThWs6JcU13HtSg))  
> thank you all SO SO much for reading and sticking with me as i wrap up this fic with first the fastest and then the slowest updates i've done. please, please, please leave a comment! i love to hear from you all!  
> and one last friendly reminder that i'm @landlessbud on tumblr - rb [this post](https://landlessbud.tumblr.com/post/621857494037299200/the-substitute-iim-david-he-mumbled-eyes-on) if you like this fic!
> 
> PS: this. might not be the last you see of this universe >:)  
> PPS: i made a [playlist](https://www.youtube.com/playlist?list=PLTVIDrrt_W16CsVbHpwzeQ26EcjAUQD4P) of all the music in this fic in the order it appears! give it a listen!


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